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

HRID 233757Notes

Reaction equation

HRID 233757 reaction equation
[CH2:1]([C:8]1[N:9]=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])=[C:15]([Br:26])[CH:14]=2)[S:11][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([O:34][C:35]([N:37]1[CH2:41][CH2:40][CH2:39][C@@H:38]1[CH:42]=[CH:43][CH2:44]O)=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH2:27]([O:34][C:35]([N:37]1[CH2:41][CH2:40][CH2:39][C@@H:38]1[CH:42]=[CH:43][CH2:44][N:19]([C:16]1[CH:17]=[CH:18][C:13]([C:10]2[S:11][CH:12]=[C:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[N:9]=2)=[CH:14][C:15]=1[Br:26])[C:20](=[O:25])[C:21]([F:22])([F:23])[F:24])=[O:36])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 197021484-(4-Benzyl-1,3-thiazol-2-yl)-2-bromo-1-trifluoroacetylaminobenzeneHCID 54485243(R)-1-(N-Benzyloxycarbonylpyrrolidin-2-yl)-3-hydroxypropene

Product 1

HCID 53803220(R)-1-(N-Benzyloxycarbonylpyrrolidin-2-yl)-3-(N-(2-bromo-4-(4-benzyl-1,3-thiazol-2-yl)phenyl)-N-trifluoroacetylamino)propeneYield 97%

Procedure

4-(4-Benzyl-1,3-thiazol-2-yl)-2-bromo-1-trifluoroacetylaminobenzene and (R)-1-(N-benzyloxycarbonylpyrrolidin-2-yl)-3-hydroxypropene were used. Chromatography using elution with a 1-5% either gradient in methylene chloride afforded the title compound (97%) as a white foam: FAB LRMS (m/z, relative intensity) 686 (MH2+, 100), 685 (MH+, 60), 684 (M+, 90), 640 (23), 578 (15), 441 (17), 371 (20); FAB HRMS calculated for [C33H29BrF3N3O3S·H]+ [with 78Br and 32S] 664.1145, found 684.1157.

Workup

  1. washelution with a 1-5% either gradient in methylene chloride

Sources & evidence

ORD record
ord-0ebd48ff713848acb4669506c9893f21
Source dataset
uspto-grants-1997_01
Patent number
US05594014

Reaction notes

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