5-Chloro-2-thiophenecarboxylic acid → HCID 58826430, compound

HRID 2244674Notes

Reaction equation

HRID 2244674 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C@H:8]([O:10][CH3:11])[C@@H:7]([NH2:12])[CH2:6]1)=[O:4].[Cl:13][C:14]1[S:18][C:17]([C:19]([OH:21])=[O:20])=[CH:16][CH:15]=1>>[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@H:8]([O:10][CH3:11])[C@@H:7]([NH:12][C:19]([C:17]2[S:18][C:14]([Cl:13])=[CH:15][CH:16]=2)=[O:20])[CH2:6]1)=[O:4].[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([O:10][CH3:11])[C@@H:7]([NH:12][C:19]([C:17]2[S:18][C:14]([Cl:13])=[CH:15][CH:16]=2)=[O:21])[CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 950485-Chloro-2-thiophenecarboxylic acidHCID 58826447HCID 58826447, compound

Product 2

HCID 58826430HCID 58826430, compoundHCID 58826460HCID 58826460, compound

Procedure

In analogy to example 10B, (3S,4S)-3-amino-4-methoxy-cyclopentanecarboxylic acid methyl ester was coupled with 5-chloro-2-thiophenecarboxylic acid. The epimers were separated by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 65:35) to give (1R,3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-methoxy-cyclopentanecarboxylic acid methyl ester and (1S,3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-methoxy-cyclopentanecarboxylic acid methyl ester, both as off-white solids. MS: 318.0 ([M+H]+).

Workup

  1. customThe epimers were separated by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 65:35)

Sources & evidence

ORD record
ord-9c81a5e9b16245329cac4ff9ec70b7ec
Source dataset
uspto-grants-2010_03
Patent number
US07678917B2

Reaction notes

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