(2S)-2-(((tert-butoxy)carbonyl)amino)-2-phenylacetic acid → ((s)-{(3,4-Dimethyl-phenyl)-[2-(5-trifluoromethyl-pyridin-2-yl)-ethyl]-carbamoyl}-phenyl-methyl)-carbamic acid tert-butyl ester

HRID 1094366Notes

Reaction equation

HRID 1094366 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[CH3:22][C:23]([O:26][C:27]([NH:29][C@H:30]([C:37](O)=[O:38])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])([CH3:25])[CH3:24]>>[C:23]([O:26][C:27](=[O:28])[NH:29][C@H:30]([C:37](=[O:38])[N:9]([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=1)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([CH3:25])([CH3:22])[CH3:24]

Participants

3

Reactant 2

HCID 11010409(2S)-2-(((tert-butoxy)carbonyl)amino)-2-phenylacetic acidHCID 58007501(3,4-Dimethyl-phenyl)-[2-(5-trifluoromethyl-pyridin-2-yl)-ethyl]-amine

Product 1

HCID 58007549((s)-{(3,4-Dimethyl-phenyl)-[2-(5-trifluoromethyl-pyridin-2-yl)-ethyl]-carbamoyl}-phenyl-methyl)-carbamic acid tert-butyl ester

Procedure

In analogy to the procedure described for the synthesis example 21, step 3, the title compound was prepared from (3,4-dimethyl-phenyl)-[2-(5-trifluoromethyl-pyridin-2-yl)-ethyl]-amine and boc-L-alpha-phenylglycine. MS (m/e): 528.3 [M+H]+.

Workup

  1. customIn analogy to the procedure described for the synthesis example 21, step 3

Sources & evidence

ORD record
ord-ce17f0032b964c4494258ee76fba690e
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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