t-Butyl (4S)-1-methyl-3-[(2R)-2-(p-toluenesulfonyloxy)propionyl]-2-oxoimidazolidine-4-carboxylate → HCID 13477732, compound

HRID 2050616Notes

Reaction equation

HRID 2050616 reaction equation
[CH3:1][N:2]1[CH2:6][C@@H:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[N:4]([C:14](=[O:28])[C@H:15](OS(C2C=CC(C)=CC=2)(=O)=O)[CH3:16])[C:3]1=[O:29].[NH2:30][C@@H:31]([CH2:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33]>>[CH3:1][N:2]1[CH2:6][C@@H:5]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[N:4]([C:14](=[O:28])[C@@H:15]([NH:30][C@H:31]([C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[CH2:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH3:16])[C:3]1=[O:29]

Participants

3

Reactant 2

HCID 14801853t-Butyl (4S)-1-methyl-3-[(2R)-2-(p-toluenesulfonyloxy)propionyl]-2-oxoimidazolidine-4-carboxylateHCID 15630398(S)-Benzyl 2-amino-4-phenylbutanoate

Product 1

HCID 13477732HCID 13477732, compoundYield 82.3%

Procedure

t-Butyl (4S)-1-methyl-3-[(2R)-2-(p-toluenesulfonyloxy)propionyl]-2-oxoimidazolidine-4-carboxylate (1 g) obtained in Example 1 - (1) and benzyl (2S)-2-amino-4-phenylbutyrate (1.55 g) were treated similarly as in Example 1 - (2) to give t-butyl (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-benzyloxycarbonyl-3-phenyl-propyl)amino]propionyl}-2-oxoimidazolidine-4-carboxylate (1.01 g) as colorless syrup. Yield: 82.3%.

Sources & evidence

ORD record
ord-c8effcb744504bdd94a6cd1e516d9b20
Source dataset
uspto-grants-1991_05
Patent number
US05013845

Reaction notes

Loading…