Valeryl chloride → (4R,5S)-3-(1'-oxopentyl)-4-methyl-5-phenyl-2-oxazolidinone

HRID 987209Notes

Reaction equation

C[C@@H]1[C@H](C2C=CC=CC=2)OC(=O)N1.C(Cl)(=O)CCCC.[O:21]=[C:22]([N:27]1[C@@H:31]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:30][O:29][C:28]1=[O:39])[CH2:23][CH2:24][CH2:25][CH3:26]>>[O:21]=[C:22]([N:27]1[C@H:31]([CH3:30])[C@H:32]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:29][C:28]1=[O:39])[CH2:23][CH2:24][CH2:25][CH3:26]

Participants

Reactant 3

HCID 61186Valeryl chloride

HCID 2733812(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone

HCID 11391341(S)-4-benzyl-3-pentanoyloxazolidin-2-one

Product 1

HCID 12109355(4R,5S)-3-(1'-oxopentyl)-4-methyl-5-phenyl-2-oxazolidinoneYield 84%

Procedure

(4R,5S)-3-(1′-oxopentyl)-4-methyl-5-phenyl-2-oxazolidinone was synthesized from (4R,5S)-4-methyl-5-phenyl-2-oxazolidinone and valeroyl chloride by the same procedure as (4S)-3-(1′-oxopentyl)-4-benzyl-2-oxazolidinone. The product (29.55 g) was obtained in 84% yield.

Sources & evidence

ORD record: ord-610e6e180d1e401a8268b090fbba3846
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06630602B1

Reaction notes

Loading…