Trifluoroacetic acid → N-(3-Amino-5-trifluoromethyl-phenyl)-N'-{(1S,2S)-1-[(2,4-dimethyl-benzylamino)-methyl]-2-hydroxy-pentyl}-malonamide

HRID 1766829Notes

Reaction equation

HRID 1766829 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:41])[CH2:20][C:21](=[O:40])[NH:22][C@@H:23]([CH2:29][NH:30][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>[NH2:7][C:8]1[CH:9]=[C:10]([NH:18][C:19](=[O:41])[CH2:20][C:21]([NH:22][C@@H:23]([CH2:29][NH:30][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])=[O:40])[CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11215504[3-(2-{(1S,2S)-1-[(2,4-dimethyl-benzylamino)-methyl]-2-hydroxy-pentylcarbamoyl}-acetylamino)-5-trifluoromethyl-phenyl]-carbamic acid tert-butyl ester

Product 1

HCID 11179439N-(3-Amino-5-trifluoromethyl-phenyl)-N'-{(1S,2S)-1-[(2,4-dimethyl-benzylamino)-methyl]-2-hydroxy-pentyl}-malonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound [3-(2-{(1S,2S)-1-[(2,4-dimethyl-benzylamino)-methyl]-2-hydroxy-pentylcarbamoyl}-acetylamino)-5-trifluoromethyl-phenyl]-carbamic acid tert-butyl ester (45 mg, 0.08 mmol, see procedure 8b above) was dissolved in CH2Cl2 (1.5 mL) and treated with TFA (0.5 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. The residue was purified by reverse-phase HPLC to afford the title compound as a white powder after lyopholization. MS found: (M+H)+=495.4.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in benzene
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-6fefa99a837e4d80a50ba91c248451f3
Source dataset
uspto-grants-2007_06
Patent number
US07230133B2

Reaction notes

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