Phenyl vinyl sulfone → HCID 53923827, compound

Participants

Reaction Steps

3-(1-Carboxycyclopentyl)-2-[2-(phenylsulphonyl)ethyl]-propanoic acid t-butyl ester was prepared following the procedure of Example 38, using as starting materials the propanoic ester of Example 35 and phenyl vinyl sulphone. The product was isolated as an oil (15%). Found: C,60.25; H,7.24. C21H30O6S. 0.13 CH2Cl2 requires C,60.24; H,7.24%. The above glutaric acid derivative was coupled with cis-3-amino-cyclohexanecarboxylic acid ethyl ester using the general procedure of Example 81 to yield 3-{1-[cis-3-ethoxycarbonyl-cyclohexyl)carbamoyl]cyclopentyl}-2-[2-(phenylsulphonyl)ethyl]propanoic acid t-butyl ester as a foam (71%). Found: C,63.53; H,8.02; N,2.38. C30H45NO7S requires C,63.91; H,8.05; N,2.48%. The above diester was treated with trifluoroacetic acid using the procedure of Example 242 to give 3-{1-[(cis-3-ethoxycarbonyl-cyclohexyl)carbamoyl]cyclopentyl}-2-8 2-(phenylsulphonyl)ethyl]propanoic acid as a foam (96%). Found: C,61.90; H,7.54; N,2.86. C26H37NO7S requires C,61.51; H,7.35; N,2.76%. The above monoester was hydrolysed using the general procedure of Example 323 to give the title diacid as a foam (95%). Found: C,59.00; H,6.83; N,2.51. C24H33NO7S. 0.5 H2O. 0.1 CH3CO2C2H5 requires C,58.92; H,7.04; N,2.81%.

Provenance & Evidence