4-(4-(4-(Trifluoromethyl)phenyl)thiazol-2-yl)benzene-1-sulfonyl chloride → trans-N-(4-(((2S,5R)-5-((R)-hydroxy(phenyl)methyl)pyrrolidin-2-yl)methyl)phenyl)-4-(4-(4-(trifluoromethyl)phenyl)thiazol-2-yl)benzenesulfonamide

HRID 887166Notes

Reaction equation

HRID 887166 reaction equation
[NH2:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][C@H:7]2[CH2:11][CH2:10][C@H:9]([C@H:12]([O:19][Si](C(C)(C)C)(C)C)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:8]2C(OC(C)(C)C)=O)=[CH:4][CH:3]=1.[F:36][C:37]([F:60])([F:59])[C:38]1[CH:43]=[CH:42][C:41]([C:44]2[N:45]=[C:46]([C:49]3[CH:54]=[CH:53][C:52]([S:55](Cl)(=[O:57])=[O:56])=[CH:51][CH:50]=3)[S:47][CH:48]=2)=[CH:40][CH:39]=1>>[OH:19][C@H:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C@@H:9]1[NH:8][C@@H:7]([CH2:6][C:5]2[CH:34]=[CH:35][C:2]([NH:1][S:55]([C:52]3[CH:53]=[CH:54][C:49]([C:46]4[S:47][CH:48]=[C:44]([C:41]5[CH:42]=[CH:43][C:38]([C:37]([F:60])([F:59])[F:36])=[CH:39][CH:40]=5)[N:45]=4)=[CH:50][CH:51]=3)(=[O:57])=[O:56])=[CH:3][CH:4]=2)[CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 112466764-(4-(4-(Trifluoromethyl)phenyl)thiazol-2-yl)benzene-1-sulfonyl chlorideHCID 57907436tert-butyl (2R,5R)-2-(4-aminobenzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidine-1-carboxylate

Product 1

HCID 53326197trans-N-(4-(((2S,5R)-5-((R)-hydroxy(phenyl)methyl)pyrrolidin-2-yl)methyl)phenyl)-4-(4-(4-(trifluoromethyl)phenyl)thiazol-2-yl)benzenesulfonamide

Procedure

The title compound was prepared from tert-butyl (2R,5R)-2-(4-aminobenzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidine-1-carboxylate (i-4b) and 4-{4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}benzenesulfonyl chloride (i-6) according to the procedure of Example 212, step A. The crude product was purified by preparative TLC plate eluting with 40% ethyl acetate in hexane to afforded the product (8.1 mg, 81%). mlz (ES) 865 (MH)+, 765 (M-Boc)+.

Workup

  1. customThe crude product was purified by preparative TLC plate
  2. washeluting with 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-be2ad791d07d4b48b71a1530bcfc2866
Source dataset
uspto-grants-2012_08
Patent number
US08247415B2

Reaction notes

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