(2S,4R)-1-(2-nitrophenyl)-4-(2-(trifluoromethyl)phenylsulfonyl)pyrrolidine-2-carboxylic acid → (2S,4R)-1-(2-Nitro-phenyl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid [(S)-1-(benzooxazole-2-carbonyl)-propyl]-amide

HRID 1025336Notes

Reaction equation

HRID 1025336 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:14][C@H:13]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]([F:27])([F:26])[F:25])(=[O:17])=[O:16])[CH2:12][C@H:11]1[C:28]([OH:30])=O)([O-:3])=[O:2].Cl.Cl.[NH2:33][C@@H:34]([CH2:46][CH3:47])[CH:35]([C:37]1[O:38][C:39]2[CH:45]=[CH:44][CH:43]=[CH:42][C:40]=2[N:41]=1)[OH:36]>>[O:38]1[C:39]2[CH:45]=[CH:44][CH:43]=[CH:42][C:40]=2[N:41]=[C:37]1[C:35]([C@@H:34]([NH:33][C:28]([C@@H:11]1[CH2:12][C@@H:13]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]([F:26])([F:25])[F:27])(=[O:16])=[O:17])[CH2:14][N:10]1[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])=[O:30])[CH2:46][CH3:47])=[O:36]

Participants

3

Reactant 2

HCID 66770587(2S,4R)-1-(2-nitrophenyl)-4-(2-(trifluoromethyl)phenylsulfonyl)pyrrolidine-2-carboxylic acidHCID 86762432(2S)-2-amino-1-(benzo[d]oxazol-2-yl)butan-1-ol dihydrochloride

Product 1

HCID 71577052(2S,4R)-1-(2-Nitro-phenyl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid [(S)-1-(benzooxazole-2-carbonyl)-propyl]-amide

Procedure

The title compound was prepared in analogy to Example 1, using (2S,4R)-1-(2-nitrophenyl)-4-(2-(trifluoromethyl)phenylsulfonyl)pyrrolidine-2-carboxylic acid (prepared as described in U.S. Pat. Appl. US20100267722) and (2S)-2-amino-1-(benzo[d]oxazol-2-yl)butan-1-ol dihydrochloride in step 1. MS (m/e)=631.15 [M+H+].

Sources & evidence

ORD record
ord-72a09f9d86dc460f81f926a20f1b6833
Source dataset
uspto-grants-2014_05
Patent number
US08729061B2

Reaction notes

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