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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1585.
Published online 2009 June 17. doi:  10.1107/S1600536809022120
PMCID: PMC2969247

N-[(2S)-4-Chloro-2-(l-menth­yloxy)-5-oxo-2,5-dihydro­furan-3-yl]-l-valine

Abstract

The title compound, C19H30ClNO5, was obtained by the tandem asymmetric Michael addition–elimination reaction of (5S)-3,4-dichloro-5-(l-menth­yloxy)furan-2(5H)-one and l-valine in the presence of potassium hydroxide. The furan­one unit is approximately planar (r.m.s. deviation = 0.0204 Å) and the six-membered cyclo­hexane ring adopts a chair conformation. The crystal structure is stabilized by a network of O—H(...)O and N—H(...)O hydrogen bonds.

Related literature

For biologically active 4-amino-2(5H)-furan­ones, see: Kimura et al. (2000 [triangle]); Tanoury et al., 2008 [triangle]). For the synthesis of the precursor, (5S)-3,4-dichloro-5-(l-menth­yloxy)furan-2(5H)-one, see: Chen & Geng (1993 [triangle]).

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Object name is e-65-o1585-scheme1.jpg

Experimental

Crystal data

  • C19H30ClNO5
  • M r = 387.89
  • Tetragonal, An external file that holds a picture, illustration, etc.
Object name is e-65-o1585-efi1.jpg
  • a = 10.4540 (4) Å
  • c = 39.300 (3) Å
  • V = 4294.9 (4) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.20 mm−1
  • T = 293 K
  • 0.30 × 0.23 × 0.15 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2004 [triangle]) T min = 0.769, T max = 0.867 (expected range = 0.860–0.970)
  • 22031 measured reflections
  • 3796 independent reflections
  • 2868 reflections with I > 2σ(I)
  • R int = 0.053

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.091
  • S = 1.04
  • 3796 reflections
  • 242 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.23 e Å−3
  • Absolute structure: Flack, (1983 [triangle]), 1499 Friedel pairs
  • Flack parameter: −0.03 (8)

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: APEX2 and SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022120/gk2204sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022120/gk2204Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The work was supported by the National Natural Science Foundation of China (grant No. 20772035) and the Natural Science Foundation of Guangdong Province, China (grant No. 5300082).

supplementary crystallographic information

Comment

Many 4-amino-2(5H)-furanones have been patented as prodrugs or insecticides and herbicides (Kimura et al., 2000; Tanoury et al., 2008). Attracted by versatility of 4-amino-2(5H)-furanones, we synthesized the title molecule with chiral synthon 3,4-dichloro-5-(S)-(l-menthyloxy)-2(5H)-furanone and L-valine in the presence of potassium hydroxide via the tandem asymmetric Michael addition-elimination reaction. With 2(5H)-furanone moiety and polyfunctional groups (carboxyl, amino, halogeno), the title compound is expected to be a biologically active product and an excellent ligand.

The structure of the title compound is illustrated in Fig. 1. The five-membered furane ring and the six-membered cyclohexane ring are connected via C10—O2—C11 ether bond. The configuration of chiral centers is following: C4(S), C10(S), C11(R), C12(S), C17(R)). The furanone unit is approximately planar, whereas the cyclohexane ring shows a chair conformation with three substituents occupying equatorial positions. The molecules are linked by O4—H6···O3 and N1—H1···O5 hydrogen bonds forming a three-dimensional network (Table. 1 and Fig. 2).

Experimental

The precursor, 3,4-dichloro-5-(S)-(L-menthyloxy)-2(5H)-furanone, was prepared according to the literature procedure (Chen et al., 1993).

After the mixture of L-valine (4.5 mmol) and potassium hydroxide (5.8 mmol) was dissolved in absolute ethyl alcohol under nitrogen atmosphere, dichloromethane solution of 3,4-dichloro-5-(S)-(l-menthyloxy)-2(5H)-furanone (3.0 mmol) was added. The reaction was carried out under the stirring at room temperature for 24 h. Once the reaction was complete, the solvents were removed under reduced pressure. The residual solid was dissolved in dichloromethane, and pH of the solution was adjusted to 3–4 with 15% of aqueous HCl solution. Then the combined organic layers from extraction were concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography with the gradient mixture of petroleum ether and ethyl acetate to give the product yielding (I) 0.6891 g (59.2%). Data for (I): [α]20°D = 47.616° (c 0.481, CH3CH2OH); 1H NMR (400 MHz, CDCl3, TMS): 0.832 (3H, d, J = 6.0 Hz, CH3), 0.904–0.935 (7H, m, CH, 2CH3), 0.955–1.057 (8H, m, 2CH3, CH2), 1.312–1.457 (2H, m, 2CH), 1.605–1.710 (2H, m, CH2), 2.100–2.350 (3H, m, CH2, CH), 3.505–3.609 (1H, m, CH), 4.726 (1H, s, NH), 5.116–5.138 (1H, d, J = 8.8 Hz, CH), 5.700 (1H, s, CH), 10.212 (1H, s, COOH); ESI-MS, m/z (%): Calcd for C19H31ClNO5+([M+H]+): 388.19, Found: 388.15 (100.0)

Refinement

All H atoms were positioned in calculated positions (O—H = 0.82 Å; N—H = 0.86 Å; C—H = 0.96Å - 0.98 Å) and were refined using a riding model, with Uiso(H) = 1.2 Ueq(C,N) for methylene, methine and amino H atoms and Uiso(H) = 1.5 Ueq(C,O) for methyl or hydroxyl H atoms.

Figures

Fig. 1.
Molecular structure of the title compound with displacement ellipsoids shown at the 30% probability level.
Fig. 2.
Perspective view of the crystal packing. Dashed lines represent hydrogen bonds.

Crystal data

C19H30ClNO5Dx = 1.200 Mg m3
Mr = 387.89Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43212Cell parameters from 3405 reflections
Hall symbol: P 4nw 2abwθ = 2.2–19.1°
a = 10.4540 (4) ŵ = 0.20 mm1
c = 39.300 (3) ÅT = 293 K
V = 4294.9 (4) Å3Block, colourless
Z = 80.30 × 0.23 × 0.15 mm
F(000) = 1664.0

Data collection

Bruker APEXII CCD area-detector diffractometer3796 independent reflections
Radiation source: fine-focus sealed tube2868 reflections with I > 2σ(I)
graphiteRint = 0.053
Detector resolution: 0 pixels mm-1θmax = 25.0°, θmin = 2.0°
[var phi] and ω scansh = −12→10
Absorption correction: multi-scan (SADABS; Bruker, 2004)k = −11→12
Tmin = 0.769, Tmax = 0.867l = −46→46
22031 measured reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040w = 1/[σ2(Fo2) + (0.0329P)2 + 0.7758P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.091(Δ/σ)max = 0.001
S = 1.04Δρmax = 0.18 e Å3
3796 reflectionsΔρmin = −0.23 e Å3
242 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc^*^=kFc[1+0.001xFc^2^λ^3^/sin(2θ)]^-1/4^
0 restraintsExtinction coefficient: 0.0020 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack, (1983), 1499 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: −0.03 (8)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C10.6886 (3)−0.0142 (2)−0.02302 (5)0.0457 (6)
C20.6349 (2)0.0184 (2)0.01161 (5)0.0434 (6)
H20.5486−0.01780.01320.052*
C30.6252 (3)0.1638 (3)0.01705 (6)0.0645 (8)
H30.61690.17710.04160.077*
C40.5046 (4)0.2198 (3)0.00080 (9)0.1066 (14)
H4A0.49290.30610.00850.160*
H4B0.43180.16920.00720.160*
H4C0.51350.2191−0.02350.160*
C50.7443 (4)0.2337 (3)0.00618 (8)0.0901 (11)
H5A0.81800.19260.01580.135*
H5B0.74030.32070.01400.135*
H5C0.75070.2325−0.01820.135*
C60.6726 (2)−0.0701 (2)0.06900 (5)0.0420 (6)
C70.5557 (2)−0.0781 (2)0.08334 (5)0.0478 (6)
C80.5677 (3)−0.1196 (2)0.11793 (5)0.0489 (6)
C90.7698 (2)−0.0992 (2)0.09642 (5)0.0429 (6)
H90.8263−0.16950.08960.052*
C100.9662 (2)−0.0054 (2)0.11656 (5)0.0445 (6)
H101.0136−0.06630.10240.053*
C110.9624 (2)−0.0546 (3)0.15302 (5)0.0529 (7)
H11A0.9221−0.13810.15340.063*
H11B0.91120.00290.16680.063*
C121.0967 (3)−0.0645 (3)0.16813 (6)0.0596 (7)
H121.1447−0.12780.15490.072*
C131.0913 (3)−0.1106 (3)0.20518 (6)0.0868 (10)
H13A1.0524−0.04580.21910.130*
H13B1.1764−0.12710.21320.130*
H13C1.0416−0.18770.20650.130*
C141.1649 (3)0.0631 (3)0.16501 (7)0.0753 (9)
H14A1.12330.12500.17970.090*
H14B1.25250.05340.17270.090*
C151.1654 (3)0.1133 (3)0.12899 (7)0.0723 (9)
H15A1.21510.05620.11470.087*
H15B1.20620.19660.12860.087*
C161.0302 (2)0.1249 (2)0.11446 (6)0.0522 (7)
H160.98280.18140.12990.063*
C171.0229 (3)0.1862 (3)0.07910 (7)0.0698 (8)
H170.93270.18460.07230.084*
C181.0627 (4)0.3269 (3)0.08046 (11)0.1295 (16)
H18A1.02130.36780.09930.194*
H18B1.03800.36850.05970.194*
H18C1.15380.33250.08320.194*
C191.0969 (4)0.1145 (4)0.05192 (7)0.1001 (12)
H19A1.18660.11770.05710.150*
H19B1.08180.15340.03020.150*
H19C1.06920.02700.05140.150*
Cl10.40649 (7)−0.05720 (10)0.066293 (16)0.0818 (3)
N10.71379 (18)−0.0411 (2)0.03775 (4)0.0463 (5)
H10.7919−0.05860.03270.056*
O10.60255 (18)0.0096 (2)−0.04637 (4)0.0835 (7)
H1A0.6322−0.0068−0.06520.125*
O20.79397 (18)−0.05167 (19)−0.02856 (4)0.0633 (5)
O30.48370 (18)−0.14530 (18)0.13838 (4)0.0625 (5)
O40.69263 (17)−0.13404 (16)0.12582 (3)0.0515 (5)
O50.83805 (15)0.01070 (15)0.10286 (4)0.0472 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0580 (17)0.0518 (16)0.0274 (11)0.0057 (12)−0.0053 (11)0.0020 (11)
C20.0501 (15)0.0544 (16)0.0259 (10)0.0075 (12)−0.0023 (10)0.0030 (10)
C30.095 (2)0.0608 (18)0.0382 (13)0.0207 (17)0.0001 (14)−0.0027 (13)
C40.135 (4)0.086 (3)0.099 (2)0.056 (2)−0.020 (2)0.002 (2)
C50.132 (3)0.067 (2)0.072 (2)−0.014 (2)0.006 (2)0.0021 (17)
C60.0515 (15)0.0469 (15)0.0276 (11)0.0046 (11)−0.0012 (11)−0.0033 (10)
C70.0480 (15)0.0655 (17)0.0301 (11)0.0041 (13)0.0008 (11)0.0020 (11)
C80.0632 (19)0.0531 (16)0.0303 (11)−0.0084 (13)0.0000 (12)−0.0034 (11)
C90.0542 (15)0.0481 (15)0.0265 (11)−0.0019 (12)−0.0016 (10)0.0020 (11)
C100.0485 (15)0.0488 (15)0.0361 (12)0.0063 (12)−0.0051 (11)−0.0040 (11)
C110.0620 (17)0.0601 (17)0.0365 (12)0.0011 (14)−0.0035 (12)−0.0009 (12)
C120.0670 (18)0.070 (2)0.0418 (13)0.0108 (15)−0.0119 (13)−0.0125 (13)
C130.106 (3)0.108 (3)0.0464 (16)0.017 (2)−0.0248 (17)−0.0055 (17)
C140.070 (2)0.092 (3)0.0641 (18)−0.0008 (18)−0.0196 (15)−0.0204 (17)
C150.064 (2)0.073 (2)0.079 (2)−0.0123 (17)−0.0053 (16)−0.0122 (17)
C160.0554 (17)0.0466 (16)0.0545 (15)0.0019 (12)0.0008 (13)−0.0082 (12)
C170.074 (2)0.0622 (19)0.0737 (19)−0.0058 (16)0.0041 (16)0.0165 (15)
C180.153 (4)0.071 (3)0.164 (4)−0.030 (3)0.003 (3)0.035 (3)
C190.119 (3)0.123 (3)0.0585 (18)0.011 (3)0.014 (2)0.019 (2)
Cl10.0488 (4)0.1483 (8)0.0483 (4)0.0136 (5)0.0026 (3)0.0132 (4)
N10.0460 (12)0.0683 (14)0.0247 (9)0.0099 (10)0.0023 (8)0.0061 (9)
O10.0698 (13)0.151 (2)0.0296 (8)0.0369 (14)−0.0086 (9)−0.0045 (11)
O20.0639 (13)0.0890 (15)0.0369 (9)0.0293 (11)0.0062 (8)0.0049 (9)
O30.0717 (13)0.0841 (14)0.0317 (8)−0.0182 (10)0.0114 (9)0.0017 (8)
O40.0601 (12)0.0674 (12)0.0270 (8)−0.0094 (9)−0.0030 (8)0.0084 (7)
O50.0530 (11)0.0463 (11)0.0422 (9)0.0000 (8)−0.0070 (8)0.0009 (8)

Geometric parameters (Å, °)

C1—O21.189 (3)C11—C121.528 (3)
C1—O11.309 (3)C11—H11A0.9700
C1—C21.511 (3)C11—H11B0.9700
C2—N11.456 (3)C12—C141.517 (4)
C2—C31.538 (3)C12—C131.534 (3)
C2—H20.9800C12—H120.9800
C3—C51.506 (4)C13—H13A0.9600
C3—C41.530 (4)C13—H13B0.9600
C3—H30.9800C13—H13C0.9600
C4—H4A0.9600C14—C151.510 (4)
C4—H4B0.9600C14—H14A0.9700
C4—H4C0.9600C14—H14B0.9700
C5—H5A0.9600C15—C161.529 (4)
C5—H5B0.9600C15—H15A0.9700
C5—H5C0.9600C15—H15B0.9700
C6—N11.336 (3)C16—C171.532 (3)
C6—C71.348 (3)C16—H160.9800
C6—C91.511 (3)C17—C191.518 (4)
C7—C81.432 (3)C17—C181.529 (4)
C7—Cl11.712 (2)C17—H170.9800
C8—O31.220 (3)C18—H18A0.9600
C8—O41.351 (3)C18—H18B0.9600
C9—O51.376 (3)C18—H18C0.9600
C9—O41.455 (3)C19—H19A0.9600
C9—H90.9800C19—H19B0.9600
C10—O51.454 (3)C19—H19C0.9600
C10—C161.520 (3)N1—H10.8600
C10—C111.523 (3)O1—H1A0.8200
C10—H100.9800
O2—C1—O1124.8 (2)C14—C12—C11109.9 (2)
O2—C1—C2125.7 (2)C14—C12—C13111.7 (2)
O1—C1—C2109.5 (2)C11—C12—C13110.9 (2)
N1—C2—C1109.21 (18)C14—C12—H12108.1
N1—C2—C3111.14 (19)C11—C12—H12108.1
C1—C2—C3111.9 (2)C13—C12—H12108.1
N1—C2—H2108.2C12—C13—H13A109.5
C1—C2—H2108.2C12—C13—H13B109.5
C3—C2—H2108.2H13A—C13—H13B109.5
C5—C3—C4112.2 (3)C12—C13—H13C109.5
C5—C3—C2112.7 (2)H13A—C13—H13C109.5
C4—C3—C2112.0 (2)H13B—C13—H13C109.5
C5—C3—H3106.5C15—C14—C12112.5 (2)
C4—C3—H3106.5C15—C14—H14A109.1
C2—C3—H3106.5C12—C14—H14A109.1
C3—C4—H4A109.5C15—C14—H14B109.1
C3—C4—H4B109.5C12—C14—H14B109.1
H4A—C4—H4B109.5H14A—C14—H14B107.8
C3—C4—H4C109.5C14—C15—C16112.0 (2)
H4A—C4—H4C109.5C14—C15—H15A109.2
H4B—C4—H4C109.5C16—C15—H15A109.2
C3—C5—H5A109.5C14—C15—H15B109.2
C3—C5—H5B109.5C16—C15—H15B109.2
H5A—C5—H5B109.5H15A—C15—H15B107.9
C3—C5—H5C109.5C10—C16—C15108.4 (2)
H5A—C5—H5C109.5C10—C16—C17113.7 (2)
H5B—C5—H5C109.5C15—C16—C17114.7 (2)
N1—C6—C7133.7 (2)C10—C16—H16106.5
N1—C6—C9119.0 (2)C15—C16—H16106.5
C7—C6—C9107.34 (18)C17—C16—H16106.5
C6—C7—C8109.7 (2)C19—C17—C18111.2 (3)
C6—C7—Cl1130.86 (17)C19—C17—C16114.0 (2)
C8—C7—Cl1119.30 (18)C18—C17—C16110.9 (3)
O3—C8—O4121.3 (2)C19—C17—H17106.8
O3—C8—C7129.0 (2)C18—C17—H17106.8
O4—C8—C7109.6 (2)C16—C17—H17106.8
O5—C9—O4110.51 (17)C17—C18—H18A109.5
O5—C9—C6108.15 (19)C17—C18—H18B109.5
O4—C9—C6104.14 (18)H18A—C18—H18B109.5
O5—C9—H9111.3C17—C18—H18C109.5
O4—C9—H9111.3H18A—C18—H18C109.5
C6—C9—H9111.3H18B—C18—H18C109.5
O5—C10—C16106.35 (18)C17—C19—H19A109.5
O5—C10—C11111.29 (19)C17—C19—H19B109.5
C16—C10—C11111.45 (19)H19A—C19—H19B109.5
O5—C10—H10109.2C17—C19—H19C109.5
C16—C10—H10109.2H19A—C19—H19C109.5
C11—C10—H10109.2H19B—C19—H19C109.5
C10—C11—C12111.4 (2)C6—N1—C2124.25 (19)
C10—C11—H11A109.4C6—N1—H1117.9
C12—C11—H11A109.4C2—N1—H1117.9
C10—C11—H11B109.4C1—O1—H1A109.5
C12—C11—H11B109.4C8—O4—C9109.00 (16)
H11A—C11—H11B108.0C9—O5—C10116.73 (18)
O2—C1—C2—N1−18.5 (4)C13—C12—C14—C15−177.1 (3)
O1—C1—C2—N1163.8 (2)C12—C14—C15—C1656.1 (3)
O2—C1—C2—C3105.0 (3)O5—C10—C16—C15179.41 (19)
O1—C1—C2—C3−72.8 (3)C11—C10—C16—C1558.0 (3)
N1—C2—C3—C576.6 (3)O5—C10—C16—C17−51.8 (3)
C1—C2—C3—C5−45.8 (3)C11—C10—C16—C17−173.2 (2)
N1—C2—C3—C4−155.9 (2)C14—C15—C16—C10−56.8 (3)
C1—C2—C3—C481.8 (3)C14—C15—C16—C17175.0 (2)
N1—C6—C7—C8177.3 (3)C10—C16—C17—C19−65.7 (3)
C9—C6—C7—C8−4.1 (3)C15—C16—C17—C1959.8 (3)
N1—C6—C7—Cl11.9 (4)C10—C16—C17—C18167.9 (3)
C9—C6—C7—Cl1−179.5 (2)C15—C16—C17—C18−66.5 (4)
C6—C7—C8—O3−175.2 (3)C7—C6—N1—C214.1 (4)
Cl1—C7—C8—O30.9 (4)C9—C6—N1—C2−164.4 (2)
C6—C7—C8—O41.9 (3)C1—C2—N1—C6−155.7 (2)
Cl1—C7—C8—O4177.94 (17)C3—C2—N1—C680.5 (3)
N1—C6—C9—O566.0 (3)O3—C8—O4—C9178.6 (2)
C7—C6—C9—O5−112.9 (2)C7—C8—O4—C91.3 (3)
N1—C6—C9—O4−176.5 (2)O5—C9—O4—C8112.3 (2)
C7—C6—C9—O44.7 (3)C6—C9—O4—C8−3.6 (2)
O5—C10—C11—C12−176.8 (2)O4—C9—O5—C1092.0 (2)
C16—C10—C11—C12−58.3 (3)C6—C9—O5—C10−154.55 (17)
C10—C11—C12—C1454.4 (3)C16—C10—O5—C9168.55 (17)
C10—C11—C12—C13178.4 (2)C11—C10—O5—C9−69.9 (2)
C11—C12—C14—C15−53.6 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.253.019 (3)148
O1—H1A···O3ii0.821.832.617 (2)160

Symmetry codes: (i) y+1, x−1, −z; (ii) −y+1/2, x−1/2, z−1/4.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2204).

References

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