2,5-Dichloro-4-(3-chlorobenzyl)thiophene-3-carboxylic acid → methyl 4-[(1S)-1-({[2,5-dichloro-4-(3-chlorobenzyl)-3-thienyl]carbonyl}amino)ethyl]benzoate

HRID 870046Notes

Reaction equation

HRID 870046 reaction equation
[Cl:1][C:2]1[S:3][C:4]([Cl:18])=[C:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)[C:6]=1[C:7]([OH:9])=O.[Cl-].[CH3:20][O:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([C@@H:30]([NH3+:32])[CH3:31])=[CH:26][CH:25]=1)=[O:23]>>[Cl:1][C:2]1[S:3][C:4]([Cl:18])=[C:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)[C:6]=1[C:7]([NH:32][C@H:30]([C:27]1[CH:28]=[CH:29][C:24]([C:22]([O:21][CH3:20])=[O:23])=[CH:25][CH:26]=1)[CH3:31])=[O:9]

Participants

3

Reactant 2

HCID 451407872,5-Dichloro-4-(3-chlorobenzyl)thiophene-3-carboxylic acidHCID 161770108[(1S)-1-(4-methoxycarbonylphenyl)ethyl]azanium chloride

Product 1

HCID 24952579methyl 4-[(1S)-1-({[2,5-dichloro-4-(3-chlorobenzyl)-3-thienyl]carbonyl}amino)ethyl]benzoate

Procedure

2,5-Dichloro-4-(3-chlorobenzyl)thiophene-3-carboxylic acid from Example 6, Step 1 (1.90 g, 5.91 mmol) was reacted with (1S)-1-[4-(methoxycarbonyl)phenyl]ethanaminium chloride from Example 1, Step 9 under conditions similar to Example 1, Step 10. The crude product was purified by Combi Flash chromatography system (2-5% EtOAc/toluene in 20 min.) to afford the desired product as a white solid. MS (−APCI): m/z 480 (M−1)−.

Workup

  1. customThe crude product was purified by Combi Flash chromatography system (2-5% EtOAc/toluene in 20 min.)

Sources & evidence

ORD record
ord-e4cccdfd942b423daf16a5021e10d79f
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

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