2-[(R)-3-[(6-isopropyl-pyridin-3-ylmethyl)-carbamoyl]-4-(4-trifluoromethoxy-benzenesulfonyl)-piperazin-1-yl]-4-methyl-thiazole-5-carboxylic acid tert-butyl ester → 2-[(R)-3-[(6-isopropyl-pyridin-3-ylmethyl)-carbamoyl]-4-(4-trifluoromethoxy-benzenesulfonyl)-piperazin-1-yl]-4-methyl-thiazole-5-carboxylic acid

HRID 908596Notes

Reaction equation

HRID 908596 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]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[C@@H:15]([C:33](=[O:45])[NH:34][CH2:35][C:36]3[CH:37]=[N:38][C:39]([CH:42]([CH3:44])[CH3:43])=[CH:40][CH:41]=3)[CH2:14]2)=[N:10][C:9]=1[CH3:46])=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[CH:42]([C:39]1[N:38]=[CH:37][C:36]([CH2:35][NH:34][C:33]([C@@H:15]2[N:16]([S:19]([C:22]3[CH:23]=[CH:24][C:25]([O:28][C:29]([F:32])([F:30])[F:31])=[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]([CH3:46])[N:10]=3)[CH2:14]2)=[O:45])=[CH:41][CH:40]=1)([CH3:44])[CH3:43]

Participants

3

Reactant 1

HCID 597038392-[(R)-3-[(6-isopropyl-pyridin-3-ylmethyl)-carbamoyl]-4-(4-trifluoromethoxy-benzenesulfonyl)-piperazin-1-yl]-4-methyl-thiazole-5-carboxylic acid tert-butyl ester

Product 1

HCID 250560612-[(R)-3-[(6-isopropyl-pyridin-3-ylmethyl)-carbamoyl]-4-(4-trifluoromethoxy-benzenesulfonyl)-piperazin-1-yl]-4-methyl-thiazole-5-carboxylic acidYield 85.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the compound (55 mg) obtained in Step 7 in trifluoroacetic acid (330 μl) was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, chloroform was added to the residue, and the mixture was concentrated again under reduced pressure. The residue was purified by thin layer chromatography (methanol:chloroform=1:10) to give the title compound (43 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, chloroform
  2. additionwas added to the residue
  3. concentrationthe mixture was concentrated again under reduced pressure
  4. customThe residue was purified by thin layer chromatography (methanol:chloroform=1:10)

Sources & evidence

ORD record
ord-b097ca330fa94f18bb7472267097d45b
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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