Trifluoroacetic acid → {(2S,3S)-2-[2-(3-amino-5-trifluoromethyl-phenylcarbamoyl)-acetylamino]-3-hydroxyhexyl}-(2,4-dimethyl-benzyl)-carbamic acid benzyl ester

HRID 1766832Notes

Reaction equation

HRID 1766832 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([NH:18][C:19](=[O:51])[CH2:20][C:21](=[O:50])[NH:22][C@@H:23]([CH2:29][N:30]([C:40]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:41])[CH2:31][C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][C:33]=2[CH3:39])[C@@H:24]([OH:28])[CH2:25][CH2:26][CH3:27])[CH:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:43]([O:42][C:40](=[O:41])[N:30]([CH2:29][C@H:23]([NH:22][C:21](=[O:50])[CH2:20][C:19](=[O:51])[NH:18][C:10]1[CH:11]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:13]=[C:8]([NH2:7])[CH:9]=1)[C@@H:24]([OH:28])[CH2:25][CH2:26][CH3:27])[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][C:33]=1[CH3:39])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69287464(3-{2-[(1S,2S)-1-{[benzyloxycarbonyl-(2,4-dimethyl-benzyl)-amino]-methyl}-2-hydroxy-pentylcarbamoyl]-acetylamino}-5-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 68616642{(2S,3S)-2-[2-(3-amino-5-trifluoromethyl-phenylcarbamoyl)-acetylamino]-3-hydroxyhexyl}-(2,4-dimethyl-benzyl)-carbamic acid benzyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (3-{2-[(1S,2S)-1-{[benzyloxycarbonyl-(2,4-dimethyl-benzyl)-amino]-methyl}-2-hydroxy-pentylcarbamoyl]-acetylamino}-5-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester (577 mg, 0.79 mmol) was dissolved in CH2Cl2 (12 mL) and treated with TFA (4 mL). The solution was stirred for 3 h and then concentrated in vacuo. The residue was dissolved in benzene and concentrated in vacuo; this procedure was repeated to provide {(2S,3S)-2-[2-(3-amino-5-trifluoromethyl-phenylcarbamoyl)-acetylamino]-3-hydroxyhexyl}-(2,4-dimethyl-benzyl)-carbamic acid benzyl ester (100% yield). MS found: (M+H)+=629.4.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in benzene
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-82c5232c0a694cb9b8881d7411602e45
Source dataset
uspto-grants-2007_06
Patent number
US07230133B2

Reaction notes

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