Hydrazine hydrate (1:1) → (2RS,5SR)-3-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acid hydrazide

HRID 890305Notes

Reaction equation

HRID 890305 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH:6]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[N:7]1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)(=[O:20])=[O:19].O.[NH2:30][NH2:31]>CO.CC1C=CC(S(O)(=O)=O)=CC=1>[F:17][C:14]1[CH:15]=[CH:16][C:11]([CH:8]2[N:7]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:6]([CH2:5][CH2:4][C:3]([NH:30][NH2:31])=[O:2])[CH2:10][CH2:9]2)=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69596717(2RS,5SR)-3-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acid methyl ester

Product 1

HCID 69596729(2RS,5SR)-3-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acid hydrazideYield 83.3%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of (2RS,5SR)-3-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acid methyl ester (1.5 g, 3.7 mmol) in MeOH (15 ml) was added hydrazine hydrate (0.54 ml, 11.1 mmol) and p-TsOH (10 mg) and the reaction mixture was heated under reflux conditions for 24 h. Evaporation and purification by column chromatography on silica gel (dichloromethane/MeOH 19:1) yielded (2RS,5SR)-3-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acid hydrazide (1.25 g, 83%) as a white solid.

Workup

  1. temperaturethe reaction mixture was heated under reflux conditions for 24 h
  2. customEvaporation and purification by column chromatography on silica gel (dichloromethane/MeOH 19:1)

Sources & evidence

ORD record
ord-90c7f54f57504490bd7916846c09a318
Source dataset
uspto-grants-2006_02
Patent number
US06995182B2

Reaction notes

Loading…