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Hydrochloric Acid → (R)-3-(4-isopropyl-benzylcarbamoyl)-4-(4-trifluoromethyl-benzenesulfonyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-carboxylic acid

HRID 908588
Notes
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Reaction equation

HRID 908588 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([S:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C@@H:13]([C:30](=[O:42])[NH:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([CH:39]([CH3:41])[CH3:40])=[CH:35][CH:34]=3)[CH2:12]2)=[N:9][CH:10]=1)=[O:4].[OH-].[Na+].Cl>O1CCCC1.CO>[CH:39]([C:36]1[CH:35]=[CH:34][C:33]([CH2:32][NH:31][C:30]([C@@H:13]2[N:14]([S:17]([C:20]3[CH:21]=[CH:22][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:25]=3)(=[O:19])=[O:18])[CH2:15][CH2:16][N:11]([C:8]3[CH:7]=[N:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][N:9]=3)[CH2:12]2)=[O:42])=[CH:38][CH:37]=1)([CH3:41])[CH3:40]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59703851(R)-3-(4-isopropyl-benzylcarbamoyl)-4-(4-trifluoromethyl-benzenesulfonyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-carboxylic acid methyl ester

Product 1

HCID 25055802(R)-3-(4-isopropyl-benzylcarbamoyl)-4-(4-trifluoromethyl-benzenesulfonyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-carboxylic acidYield 83.3%

Reagents, catalysts & solvents

2
HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of the compound (75 mg) obtained in Example 8 in tetrahydrofuran (400 μl) and methanol (400 μl) was added, with stirring at room temperature, 2N aqueous sodium hydroxide solution (186 μl). After stirring at room temperature for 30 min, 2N aqueous hydrochloric acid solution (186 μl) was added, and the mixture was concentrated under reduced pressure. Methanol and water were 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 (61 mg).

Workup

  1. stirringAfter stirring at room temperature for 30 min
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionMethanol and water were added to the residue
  4. stirringthe mixture was stirred at room temperature
  5. filtrationThe precipitated crystals were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-d6743426456f4c32bdecbd9493c750c7
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