5-Chloro-2-thiophenecarboxylic acid → (2S,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

HRID 1162620Notes

Reaction equation

HRID 1162620 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:18])[C@@H:5]1[CH2:9][C@@H:8]([NH2:10])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[Cl:19][C:20]1[S:24][C:23]([C:25](O)=[O:26])=[CH:22][CH:21]=1>>[CH3:2][O:3][C:4]([C@@H:5]1[CH2:9][C@@H:8]([NH:10][C:25]([C:23]2[S:24][C:20]([Cl:19])=[CH:21][CH:22]=2)=[O:26])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])=[O:18]

Participants

3

Reactant 2

HCID 950485-Chloro-2-thiophenecarboxylic acidHCID 17750455Methyl (2S,4R)-4-aminopyrrolidine-2-carboxylate hydrochloride, N1-BOC protected

Product 1

HCID 42643336(2S,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Procedure

11.1 Using general procedure D N-Boc-trans-4-amino-L-proline methyl ester hydrochloride was coupled with 5-chlorothiophene-2-carboxylic acid to give (2S,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester. White solid. MS 389.4 ([M+H]+)

Sources & evidence

ORD record
ord-c3cf40ceb80b4c0eadb283842b932072
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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