Triethylamine → 3-(2-Methyl-pent-2-enoyl)-4-phenyl-oxazolidin-2-one

HRID 349823

Reaction equation

F[C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10]C(O)=O.[CH3:14][C:15]([CH3:20])(C)[C:16](Cl)=[O:17].[Li+].[Cl-].C[C@H]1[C@@H](C2C=CC=CC=2)[O:27][C:26](=[O:35])[NH:25]1.[CH2:36](N(CC)CC)[CH3:37]>C1COCC1>[CH3:14][C:15](=[CH:20][CH2:36][CH3:37])[C:16]([N:25]1[CH:9]([C:3]2[CH:2]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:10][O:35][C:26]1=[O:27])=[O:17]

Participants

Conditions

Temperature: 0 °C

Procedure

A flask was charged with 29.5 g (158 mmol) of 3-(2,4-difluoro-phenyl)-propionic acid, 700 mL of THF, and 82.8 mL of triethylamine. The mixture was cooled to 0° C. and 23.4 mL of trimethyl acetyl chloride was added slowly. The mixture was stirred cold for 1 hour. Then 8.06 g (190 mmol) of LiCl and 28.1 g of (4S,5R)-4-methyl-5-phenyl-oxazolidin-2-one was added. The mixture was allowed to warm room temperature and stirred overnight. The solids were filtered off, and the solvent was removed under reduced pressure. The residue was taken up in diethyl ether and washed with sat. aq. ammonium chloride, sat. aq. sodium bicarbonate, and the solvent were removed under reduced pressure. The crude residue was purified by column chromatography (3:1 dichloromethane/hexanes eluent) to give 54 g (99% yield) of the titled compound.

Workup

temperatureto warm room temperature
stirringstirred overnight
filtrationThe solids were filtered off
customthe solvent was removed under reduced pressure
washwashed with sat. aq. ammonium chloride, sat. aq. sodium bicarbonate
customthe solvent were removed under reduced pressure
customThe crude residue was purified by column chromatography (3:1 dichloromethane/hexanes eluent)

Sources & evidence

ORD record: ord-b24b07d8b7dc45fb9b56dd08ab118735
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179934B2

Linked notes

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