Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1) → (RS,SR)-2-benzenesulfonyl-2-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-propionic acid methyl ester

HRID 602749Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:21])[C:4]([S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])([CH:6]1[CH2:10][CH2:9][C:8](=O)[CH2:7]1)[CH3:5].Cl.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30]N)=[CH:26][CH:25]=1.C([O-])(O)=O.[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:21])[C:4]([S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])([CH:6]1[CH2:10][C:9]2[NH:30][C:27]3[CH:26]=[CH:25][C:24]([Cl:23])=[CH:29][C:28]=3[C:8]=2[CH2:7]1)[CH3:5]

Participants

Conditions

Temperature: 70 °C

Procedure

To 100 mg (0.32 mmol) of (RS,SR)-2-benzenesulfonyl-2-(3-oxo-cyclopentyl)-propionic acid methyl ester in glacial acetic acid (3 mL), 63 mg (0.35 mmol, 1.1 eq) of (4-chloro-phenyl)-hydrazine hydrochloride were added and the reaction mixture was heated at 70° C. for about 5 hours. Until completion, the reaction was monitored by HPLC and TLC. 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 1:1 followed by a trituration with Et2O yielded 45 mg (34%) of (RS,SR)-2-benzenesulfonyl-2-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-propionic acid methyl ester as a light yellow solid, MS: 418 (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-d73ab590947540b2b2848e1de645f628
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906546B2

Reaction notes

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