Methyl 2-bromopropionate → HCID 66652902, compound

HRID 572589Notes

Reaction equation

HRID 572589 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([CH:26]([NH2:28])[CH3:27])=[CH:22][CH:21]=3)[N:16]=2)=[CH:11][C:10]=1[C:29]([F:32])([F:31])[F:30].Br[CH:34]([CH3:39])[C:35]([O:37][CH3:38])=[O:36]>>[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([CH:26]([NH:28][C@H:34]([C:35]([O:37][CH3:38])=[O:36])[CH3:39])[CH3:27])=[CH:22][CH:21]=3)[N:16]=2)=[CH:11][C:10]=1[C:29]([F:31])([F:32])[F:30].[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([C@@H:26]([NH:28][C@@H:34]([C:35]([O:37][CH3:38])=[O:36])[CH3:39])[CH3:27])=[CH:22][CH:21]=3)[N:16]=2)=[CH:11][C:10]=1[C:29]([F:31])([F:32])[F:30].[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([C@H:26]([NH:28][C@H:34]([C:35]([O:37][CH3:38])=[O:36])[CH3:39])[CH3:27])=[CH:22][CH:21]=3)[N:16]=2)=[CH:11][C:10]=1[C:29]([F:31])([F:32])[F:30].[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([C@H:26]([NH:28][C@@H:34]([C:35]([O:37][CH3:38])=[O:36])[CH3:39])[CH3:27])=[CH:22][CH:21]=3)[N:16]=2)=[CH:11][C:10]=1[C:29]([F:31])([F:32])[F:30]

Participants

6

Reactant 2

HCID 95576Methyl 2-bromopropionateHCID 131732828HCID 131732828, compound

Product 4

HCID 66652778HCID 66652778, compoundHCID 66652827HCID 66652827, compoundHCID 66652902HCID 66652902, compoundYield 33%HCID 66652909HCID 66652909, compoundYield 31%

Procedure

Methyl N-[1-(4-{5-[2′-methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]-alaninate was prepared following the general procedure 11 starting from 1-(4-{5-[2′-methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethanamine, hydrochloride salt and methyl 2-bromopropionate. The resulting pair of two diastereomers could be separated by flash chromatography (heptane/EtOAc gradient from 95:5 up to 85:15), affording methyl N-[(1S)-1-(4-{5-[2′-methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]-D-alaninate and methyl N-[(1R)-1-(4-{5-[2′-methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]-L-alaninate (90 mg, 33%) as a first fraction and methyl N-[(1S)-1-(4-{5-[2′-methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]-L-alaninate and methyl N-[(1R)-1-(4-{5-[2′-methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]-D-alaninate (85 mg, 31%) as second fraction.

Workup

  1. customThe resulting pair of two diastereomers could be separated by flash chromatography (heptane/EtOAc gradient from 95:5 up to 85:15)

Sources & evidence

ORD record
ord-a15588911e3145adbc85395a936c7502
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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