4-(3-Chlorobenzyl)thiophene-3-carboxylic acid → methyl 4-[(1S)-1-({[4-(3-chlorobenzyl)-3-thienyl]carbonyl}amino)ethyl]benzoate

HRID 870042Notes

Reaction equation

HRID 870042 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][C:6]1[C:7]([C:11]([OH:13])=O)=[CH:8][S:9][CH:10]=1.[Cl-].[CH3:18][O:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([C@@H:28]([NH3+:30])[CH3:29])=[CH:24][CH:23]=1)=[O:21]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][C:6]1[C:7]([C:11]([NH:30][C@H:28]([C:25]2[CH:26]=[CH:27][C:22]([C:20]([O:19][CH3:18])=[O:21])=[CH:23][CH:24]=2)[CH3:29])=[O:13])=[CH:8][S:9][CH:10]=1

Participants

3

Reactant 2

HCID 451405894-(3-Chlorobenzyl)thiophene-3-carboxylic acidHCID 161770108[(1S)-1-(4-methoxycarbonylphenyl)ethyl]azanium chloride

Product 1

HCID 45140964methyl 4-[(1S)-1-({[4-(3-chlorobenzyl)-3-thienyl]carbonyl}amino)ethyl]benzoate

Procedure

4-(3-Chlorobenzyl)thiophene-3-carboxylic acid from Example 3, Step 3 (380 mg, 1.50 mmol) was reacted with (1S)-1-[4-(methoxycarbonyl)phenyl]ethanaminium chloride from Example 1, Step 9 under conditions similar to Example 1, Step 10. After chromatography on silica gel (EtOAc/hexane 40:60 to 95:5), the desired product was obtained as a white solid.

Sources & evidence

ORD record
ord-7d892b080f54498bb28d9bb3c3524b15
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

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