Reacción #790331

ord-5479a3957af04f848dd8e8678f3283ee

Ecuación de reacción

COc1ccc(S(=O)(=O)NCCCCCSC(C)(C)C(=O)O)cc1
8-(4-Methoxybenzenesulphonamido)-2,2-dimethyl-3-thiaoctanoic acid
CCOC(=O)C(C)(C)SCCCCCBr
ethyl 8-bromo-2,2-dimethyl-3-thiaoctanoate
COc1ccc(S(N)(=O)=O)cc1
4-methoxybenzenesulphonamide
CCOC(=O)C(C)(C)SCCCCCNS(=O)(=O)c1ccc(OC)cc1
ethyl 8-(4-methoxybenzenesulphonamido)-2,2-dimethyl-3-thiaoctanoate
Rendimiento 69.0%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroIn an analogous way, there are obtained

Procedimiento

In an analogous way, there are obtained: 2. 8-(4-Methoxybenzenesulphonamido)-2,2-dimethyl-3-thiaoctanoic acid by reaction of ethyl 8-bromo-2,2-dimethyl-3-thiaoctanoate with 4-methoxybenzenesulphonamide to give (a) ethyl 8-(4-methoxybenzenesulphonamido)-2,2-dimethyl-3-thiaoctanoate; after chromatography on silica gel/cyclohexane+diethyl ether (2:1 v/v), the yield is 69% of theory; colourless oil; nD20 =1.5280 and subsequent saponification of this ester to give (b) the desired acid; yield 90% of theory; m.p. 57°-59° C. 3. 8-(3-Trifluoromethylbenzenesulphonamido)-2,2-dimethyl-3-thiaoctanoic acid by reaction of ethyl 8-bromo-2,2-dimethyl-3-thiaoctanoate with 3-trifluoromethylbenzenesulphonamide to give

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04981873uspto-grants-1991_01