Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1) → (RS,SR)-benzenesulfonyl-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-fluoro-acetic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]([S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14])([F:12])[CH:5]1[CH2:10][CH2:9][CH2:8][C:7](=O)[CH2:6]1.Cl.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31]N)=[CH:27][CH:26]=1.C([O-])(O)=O.[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:22])[C:4]([S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14])([CH:5]1[CH2:10][CH2:9][C:8]2[C:29]3[C:28](=[CH:27][CH:26]=[C:25]([Cl:24])[CH:30]=3)[NH:31][C:7]=2[CH2:6]1)[F:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To 1.70 g (5.2 mmol) (RS,SR)-benzenesulfonyl-fluoro-(3-oxo-cyclohexyl)-acetic acid methyl ester in glacial acetic acid (20 mL), 1.05 g (5.72 mmol, 1.1 eq) of (4-chloro-phenyl)-hydrazine hydrochloride were added and the reaction mixture was stirred at 40° C. over night. An aqueous solution of NaHCO3 was added until pH=7 was reached, and the mixture was extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated. A column chromatography on silica gel with heptane/EtOAc 2:1 followed by a trituration from Et2O yielded 1.56 g (70%) of (RS,SR)-benzenesulfonyl-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-fluoro-acetic acid methyl ester as a white solid, MS: 436 (MH+).
Workup
- extractionthe mixture was extracted with EtOAc
- dry with materialThe combined organic phases were dried over Na2SO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-256778ddf49349639d9df20b84ca5f02
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07906546B2
Reaction notes
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