2-[(R)-3-(4-isopropyl-benzylcarbamoyl)-4-(4-trifluoromethyl-benzenesulfonyl)-piperazin-1-yl]-4-methyl-thiazole-5-carboxylic acid tert-butyl ester → 2-[(R)-3-(4-isopropyl-benzylcarbamoyl)-4-(4-trifluoromethyl-benzenesulfonyl)-piperazin-1-yl]-4-methyl-thiazole-5-carboxylic acid

HRID 908585Notes

Reaction equation

HRID 908585 reaction equation
C([O:5][C:6]([C:8]1[S:12][C:11]([N:13]2[CH2:18][CH2:17][N:16]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[C@@H:15]([C:32](=[O:44])[NH:33][CH2:34][C:35]3[CH:40]=[CH:39][C:38]([CH:41]([CH3:43])[CH3:42])=[CH:37][CH:36]=3)[CH2:14]2)=[N:10][C:9]=1[CH3:45])=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[CH:41]([C:38]1[CH:37]=[CH:36][C:35]([CH2:34][NH:33][C:32]([C@@H:15]2[N:16]([S:19]([C:22]3[CH:23]=[CH:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=3)(=[O:21])=[O:20])[CH2:17][CH2:18][N:13]([C:11]3[S:12][C:8]([C:6]([OH:7])=[O:5])=[C:9]([CH3:45])[N:10]=3)[CH2:14]2)=[O:44])=[CH:40][CH:39]=1)([CH3:43])[CH3:42]

Participants

3

Reactant 1

HCID 250557992-[(R)-3-(4-isopropyl-benzylcarbamoyl)-4-(4-trifluoromethyl-benzenesulfonyl)-piperazin-1-yl]-4-methyl-thiazole-5-carboxylic acid tert-butyl ester

Product 1

HCID 250558002-[(R)-3-(4-isopropyl-benzylcarbamoyl)-4-(4-trifluoromethyl-benzenesulfonyl)-piperazin-1-yl]-4-methyl-thiazole-5-carboxylic acidYield 47.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the compound (224 mg) obtained in Example 5 in trifluoroacetic acid (1.1 ml) was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, toluene was added to the residue, and the mixture was concentrated again under reduced pressure. Diisopropyl ether was added to the residue, and the mixture was stirred at room temperature. The precipitated crystals were collected by filtration, and dried to give the title compound (97 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, toluene
  2. additionwas added to the residue
  3. concentrationthe mixture was concentrated again under reduced pressure
  4. additionDiisopropyl ether was added to the residue
  5. filtrationThe precipitated crystals were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-9576f7dcd28c44bb8d0b9c77342d900c
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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