4-(3-Benzyl-1,2,4-oxadiazol-5-ylmethyl)-2-bromo-1-trifluoroacetylaminobenzene → (R)-1(N-Benzyloxycarbonylpyrrolidin-2-yl)-3-(N-(2-bromo-4-(3-benzyl-1,2,4-oxadiazol-5-ylmethyl)phenyl)-N-trifluoroacetylamino)propene

HRID 862175Notes

Reaction equation

HRID 862175 reaction equation
[CH2:1]([C:8]1[N:12]=[C:11]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])=[C:16]([Br:27])[CH:15]=2)[O:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([O:35][C:36]([N:38]1[CH2:42][CH2:41][CH2:40][C@@H:39]1[CH:43]=[CH:44][CH2:45]O)=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH2:28]([O:35][C:36]([N:38]1[CH2:42][CH2:41][CH2:40][C@@H:39]1[CH:43]=[CH:44][CH2:45][N:20]([C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C:11]2[O:10][N:9]=[C:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:12]=2)=[CH:15][C:16]=1[Br:27])[C:21](=[O:26])[C:22]([F:25])([F:23])[F:24])=[O:37])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

3

Reactant 2

HCID 197021404-(3-Benzyl-1,2,4-oxadiazol-5-ylmethyl)-2-bromo-1-trifluoroacetylaminobenzeneHCID 54485243(R)-1-(N-Benzyloxycarbonylpyrrolidin-2-yl)-3-hydroxypropene

Product 1

HCID 54350671(R)-1(N-Benzyloxycarbonylpyrrolidin-2-yl)-3-(N-(2-bromo-4-(3-benzyl-1,2,4-oxadiazol-5-ylmethyl)phenyl)-N-trifluoroacetylamino)propeneYield 90%

Procedure

4-(3-Benzyl-1,2,4-oxadiazol-5-ylmethyl)-2-bromo-1-trifluoroacetylaminobenzene and (R)-1-(N-benzyloxycarbonylpyrrolidin-2-yl)-3-hydroxypropene were used. Chromatography using elution with 5% either in methylene chloride afforded the title compound (90%) as a thick yellow oil: Rf =0.75 (CHCl3 --CH3OH 20:1); LRMS (m/z, relative intensity) 683 (M+,18).

Workup

  1. washelution with 5%

Sources & evidence

ORD record
ord-03e95b20f0e24067a3272dcfd2cfebf8
Source dataset
uspto-grants-1998_02
Patent number
US05717102

Reaction notes

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