5-Chloro-2-thiophenecarboxylic acid → (3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1162633Notes

Reaction equation

HRID 1162633 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[C@@H:10]([NH2:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[S:20][C:19]([C:21](O)=[O:22])=[CH:18][CH:17]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[C@@H:10]([NH:14][C:21]([C:19]2[S:20][C:16]([Cl:15])=[CH:17][CH:18]=2)=[O:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 950485-Chloro-2-thiophenecarboxylic acidHCID 104654571-Boc-(3S,4S)-3-amino-4-hydroxypyrrolidine

Product 1

HCID 42643219(3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Procedure

22.4 Using general procedure C (3S,4S)-3-amino-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester was reacted with 5-chlorothiophene-2-carboxylic acid to give (3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester. Off-white solid. MS 347.3 ([M+H]+)

Sources & evidence

ORD record
ord-fc7edb41a0ef4171b02f194aa2f92049
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

Loading…