1,2-Oxazole-5-carboxylic acid → 3-Chloro-3'-fluoro-4'-[(R)-1-({3-[(isoxazole-5-carbonyl)-amino]-oxetane-3-carbonyl}-amino)-ethyl]-biphenyl-2-carboxylic acid methyl ester

HRID 1404570Notes

Reaction equation

HRID 1404570 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([C:12]2[CH:17]=[CH:16][C:15]([C@H:18]([NH:20][C:21]([C:23]3([NH2:27])[CH2:26][O:25][CH2:24]3)=[O:22])[CH3:19])=[C:14]([F:28])[CH:13]=2)=[CH:7][CH:8]=[CH:9][C:10]=1[Cl:11])=[O:4].[O:29]1[C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=[N:30]1>>[CH3:1][O:2][C:3]([C:5]1[C:6]([C:12]2[CH:17]=[CH:16][C:15]([C@H:18]([NH:20][C:21]([C:23]3([NH:27][C:34]([C:33]4[O:29][N:30]=[CH:31][CH:32]=4)=[O:35])[CH2:24][O:25][CH2:26]3)=[O:22])[CH3:19])=[C:14]([F:28])[CH:13]=2)=[CH:7][CH:8]=[CH:9][C:10]=1[Cl:11])=[O:4]

Participants

3

Reactant 2

HCID 20605991,2-Oxazole-5-carboxylic acidHCID 679794974'-{(R)-1-[(3-Amino-oxetane-3-carbonyl)-amino]-ethyl}-3-chloro-3'-fluoro-biphenyl-2-carboxylic acid methyl ester

Product 1

HCID 573828363-Chloro-3'-fluoro-4'-[(R)-1-({3-[(isoxazole-5-carbonyl)-amino]-oxetane-3-carbonyl}-amino)-ethyl]-biphenyl-2-carboxylic acid methyl ester

Procedure

The title compound was prepared in analogy to example 1 using intermediate 4 instead of intermediate 1 and isoxazole-5-carboxylic acid instead of 3-fluoro-5-(trifluoromethyl)benzoic acid and was obtained as white solid. MS: 502.1 [M+H]+.

Workup

  1. customwas obtained as white solid

Sources & evidence

ORD record
ord-5815a39314ce4ef2897c488d7eb4052b
Source dataset
uspto-grants-2014_12
Patent number
US08912221B2

Reaction notes

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