Triethylamine → (4R,5S)-3-((R)-6-Cyclohexyl-4-methyl-hexanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

HRID 132631Notes

Reaction equation

[CH:1]1([CH2:7][CH2:8][C@@H:9]([CH3:15])[CH2:10][CH2:11][C:12]([OH:14])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[CH3:30][C@@H:31]1[C@H:35]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[O:34][C:33](=[O:42])[NH:32]1.[Cl-].[Li+]>C1COCC1>[CH:1]1([CH2:7][CH2:8][C@@H:9]([CH3:15])[CH2:10][CH2:11][C:12]([N:32]2[C@H:31]([CH3:30])[C@H:35]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[O:34][C:33]2=[O:42])=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

A flask was charged with 4.17 g (19.6 mmol) of (R)-6-cyclohexyl-4-methyl-hexanoic acid, 40 mL of THF, and 8.56 mL (61.4 mmol) of triethylamine. The mixture was cooled in a 0° C. bath, and 2.41 mL (19.6 mmol) of pivaloyl chloride was added. The mixture was stirred for 1 h at 0° C. Then 2.79 g (16.4 mmol) of (4R,5S)-4-methyl-5-phenyl-2-oxazolidinone and 0.823 g (19.6 mmol) of lithium chloride were added as solids. The mixture was allowed to warm to room temperature and stirred overnight. The resulting solids were filtered off. The solvent was stripped under reduce pressure, and the residue was purified by column chromatography (eluent: 4:1 hexanes/ethyl acetate) to give 6.09 g (quant.) of a clear oil: 1H NMR (400 MHz, CDCl3) δ ppm 0.89 (m, 8H) 1.16 (m, 6H) 1.68 (m, 9H) 2.87 (m, 1H) 2.99 (m, 1H) 4.76 (qd, J=6.83, 6.59 Hz, 1H) 5.66 (d, J=7.32 Hz, 1H) 7.30 (m, 2H) 7.40 (m, 3H). MS (APCI) m+1/z=372.

Workup

temperatureto warm to room temperature
stirringstirred overnight
filtrationThe resulting solids were filtered off
customthe residue was purified by column chromatography (eluent: 4:1 hexanes/ethyl acetate)
customto give 6.09 g (quant.) of a clear oil

Sources & evidence

ORD record: ord-45f98210d5054df89e1edc424d1b1706
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07388023B2

Reaction notes

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