3-Cyclopentylpropionyl chloride → (4S)-benzyl-3-(3-cyclopentylpropanoyl)oxazolidin-2-one

HRID 653967Notes

Reaction equation

HRID 653967 reaction equation
[CH:1]1([CH2:6][CH2:7][C:8](Cl)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:11]1([CH2:17][C@H:18]2[CH2:22][O:21][C:20](=[O:23])[NH:19]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH:1]1([CH2:6][CH2:7][C:8]([N:19]2[C@@H:18]([CH2:17][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:22][O:21][C:20]2=[O:23])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 660393-Cyclopentylpropionyl chlorideHCID 736225(S)-4-Benzyl-2-oxazolidinone

Product 1

HCID 11077479(4S)-benzyl-3-(3-cyclopentylpropanoyl)oxazolidin-2-oneYield 96.6%

Procedure

Following the procedure described in Example 45, 6.4 g of cyclopentane propionyl chloride and 7.1 g of (S)-4-phenylmethyl-2-oxazolidinone yielded 11.6 g of (S)-3-[3-cyclopentyl-1-oxopropyl]-4-(phenylmethyl)-2-oxazolidinone. [α]D25 =+99.61°

Sources & evidence

ORD record
ord-67b6e06b86c344518f83cfcb83a74774
Source dataset
uspto-grants-1992_07
Patent number
US05128448

Reaction notes

Loading…