Methyl 2-bromopropionate → HCID 66652762, compound

HRID 572588Notes

Reaction equation

HRID 572588 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[C:7]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH:20]([NH2:22])[CH3:21])=[CH:16][CH:15]=3)[N:10]=2)[CH:6]=[CH:5][C:4]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=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]=[C:7]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:15]=[CH:16][C:17]([CH:20]([NH:22][C@H:34]([C:35]([O:37][CH3:38])=[O:36])[CH3:39])[CH3:21])=[CH:18][CH:19]=3)[N:10]=2)[CH:6]=[CH:5][C:4]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]([F:32])([F:31])[F:30].[CH3:2][C:3]1[CH:8]=[C:7]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:15]=[CH:16][C:17]([C@@H:20]([NH:22][C@@H:34]([C:35]([O:37][CH3:38])=[O:36])[CH3:39])[CH3:21])=[CH:18][CH:19]=3)[N:10]=2)[CH:6]=[CH:5][C:4]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]([F:32])([F:31])[F:30].[CH3:2][C:3]1[CH:8]=[C:7]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:15]=[CH:16][C:17]([C@H:20]([NH:22][C@H:34]([C:35]([O:37][CH3:38])=[O:36])[CH3:39])[CH3:21])=[CH:18][CH:19]=3)[N:10]=2)[CH:6]=[CH:5][C:4]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]([F:32])([F:31])[F:30].[CH3:2][C:3]1[CH:8]=[C:7]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:15]=[CH:16][C:17]([C@H:20]([NH:22][C@@H:34]([C:35]([O:37][CH3:38])=[O:36])[CH3:39])[CH3:21])=[CH:18][CH:19]=3)[N:10]=2)[CH:6]=[CH:5][C:4]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]([F:32])([F:31])[F:30]

Participants

6

Reactant 2

HCID 95576Methyl 2-bromopropionateHCID 131732827HCID 131732827, compound

Product 4

HCID 66652762HCID 66652762, compoundYield 27%HCID 66652877HCID 66652877, compoundHCID 66652904HCID 66652904, compoundYield 18%HCID 86683839HCID 86683839, compound

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 (Example 23, step 2) and methyl 2-bromopropionate. The resulting pair of two diastereomers was 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 (75 mg, 27%) as one 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 (50 mg, 18%) as a second fraction.

Workup

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

Sources & evidence

ORD record
ord-1488df73ee344ac48311b4d05d9dc1db
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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