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Trifluoroacetic acid → 2-[(R)-4-(2-fluoro-4-trifluoromethoxy-benzenesulfonyl)-3-(4-propyl-benzylcarbamoyl)-piperazin-1-yl]-4-methyl-thiazole-5-carboxylic acid

HRID 908602
Notes
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Reaction equation

HRID 908602 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][C:23]=3[F:33])(=[O:21])=[O:20])[C@@H:15]([C:34](=[O:46])[NH:35][CH2:36][C:37]3[CH:42]=[CH:41][C:40]([CH2:43][CH2:44][CH3:45])=[CH:39][CH:38]=3)[CH2:14]2)=[N:10][C:9]=1[CH3:47])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[F:33][C:23]1[CH:24]=[C:25]([O:28][C:29]([F:30])([F:31])[F:32])[CH:26]=[CH:27][C:22]=1[S:19]([N:16]1[CH2:17][CH2:18][N:13]([C:11]2[S:12][C:8]([C:6]([OH:7])=[O:5])=[C:9]([CH3:47])[N:10]=2)[CH2:14][C@@H:15]1[C:34](=[O:46])[NH:35][CH2:36][C:37]1[CH:38]=[CH:39][C:40]([CH2:43][CH2:44][CH3:45])=[CH:41][CH:42]=1)(=[O:20])=[O:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 597037082-[(R)-4-(2-fluoro-4-trifluoromethoxy-benzenesulfonyl)-3-(4-propyl-benzylcarbamoyl)-piperazin-1-yl]-4-methyl-thiazole-5-carboxylic acid tert-butyl ester

Product 1

HCID 597037632-[(R)-4-(2-fluoro-4-trifluoromethoxy-benzenesulfonyl)-3-(4-propyl-benzylcarbamoyl)-piperazin-1-yl]-4-methyl-thiazole-5-carboxylic acidYield 82.9%

Reagents, catalysts & solvents 1

HCID 6212
Chloroform
Solvent

Procedure

To a solution of the compound (59 mg) obtained in Step 7 in chloroform (0.3 ml) was added, with stirring at room temperature, trifluoroacetic acid (0.3 ml). After stirring at room temperature for 7 hr, the reaction mixture was concentrated under reduced pressure, toluene was added to the residue, and the mixture was concentrated again under reduced pressure. The residue was purified by column chromatography (ethyl acetate:n-hexane=1:2-10% methanol/chloroform) to give the title compound (45 mg).

Workup

  1. stirringAfter stirring at room temperature for 7 hr
  2. concentrationthe reaction mixture was concentrated under reduced pressure, toluene
  3. additionwas added to the residue
  4. concentrationthe mixture was concentrated again under reduced pressure
  5. customThe residue was purified by column chromatography (ethyl acetate:n-hexane=1:2-10% methanol/chloroform)

Sources & evidence

ORD record
ord-e24294657e804f4c9476d735636ceaf3
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08017612B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes