Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1) → HCID 11419051, compound

HRID 602742Notes

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])([CH:6]1[CH2:11][CH2:10][CH2:9][C:8](=O)[CH2:7]1)[CH3:5].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:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)(=[O:15])=[O:14])([CH:6]1[CH2:11][CH2:10][C:9]2[C:29]3[C:28](=[CH:27][CH:26]=[C:25]([Cl:24])[CH:30]=3)[NH:31][C:8]=2[CH2:7]1)[CH3:5]

Participants

Conditions

Temperature: 40 °C

Procedure

To 0.14 g (0.43 mmol) (RS,SR)-2-benzenesulfonyl-2-(3-oxo-cyclohexyl)-propionic acid methyl ester in glacial acetic acid (3 mL), 88 mg (0.47 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 with Et2O yielded 187 mg (65%) of (RS,SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propionic acid methyl ester as a white solid, MS: 432 (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-a4e5bb0079a44d0e92ca80a00c344f6a
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906546B2

Reaction notes

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