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ChemicalBook CAS DataBase List 3-{[(4-CHLOROPHENYL)SULFONYL]AMINO}PROPANOIC ACID
36974-65-9

3-{[(4-CHLOROPHENYL)SULFONYL]AMINO}PROPANOIC ACID synthesis

3synthesis methods
-

Yield:36974-65-9 64%

Reaction Conditions:

with sodium hydroxide in water at 35; pH=Ca.9; for 1 h;

Steps:

S.3 General method for the preparation of 3-arylsulfonylamino propionic acids 10

General procedure: To partially dissolved β-alanine (9) (0.6 g, 6.8 mmol) in distilled water (4 mL) was added a solution ofaqueous NaOH 2M (3.4 mL), followed by the portionwise addition of the different arylsulfonyl chloride2a-h, l (9.6 mmol). The reaction mixture was stirred at 35 °C and a solution of 1 M aqueous NaOH wasadded portionwise to maintain a pH of approximately 9. After complete consumption of alkali, stirringwas continued at 35 °C for an additional 1 h. Unreacted arylsulfonyl chloride was removed by filtration,and the reaction mixture was acidified with 5M aqueous HCl at 0 °C to pH 2. The aqueous solution withsolid precipitate was stored at 4 °C o.n. The crystals formed were collected by filtration, washed withcold water and dried at reduced pressure.S3.1 3-(4-Chloro-benzenesulfonylamino)-propionic acid (10a) [S12]Obtained in 64% yield as a white solid.

References:

Bassetto, Marcella;Leyssen, Pieter;Neyts, Johan;Yerukhimovich, Mark M.;Frick, David N.;Courtney-Smith, Matthew;Brancale, Andrea [European Journal of Medicinal Chemistry,2017,vol. 125,p. 1115 - 1131] Location in patent:supporting information