HCID 86752039, compound → HCID 19700371, compound

Participants

Reaction Steps

A The process is performed as in Example 2A, but starting with 3.4 g of tert-butyl (2RS,4SR,5RS)-1-{2-[3-(3-benzyloxycarbonylphenyl)ureido]acetyl}-5-(2-fluorophenyl)-4-methylsulphonyl-2-pyrrolidinecarboxylate, 0.3 g of 10% palladium-on-charcoal and 100 cm3 of ethanol under a hydrogen atmosphere (130 kPa). After treatment, 2.4 g of (2RS,4SR,5RS)-3-(3-{2-[2-tert-butoxycarbonyl-5-(2-fluorophenyl)-4-methylsulphonyl-1-pyrrolidinyl]-2-oxoethyl}ureido)benzoic acid are obtained [Rf=0.3; eluent: methylene chloride/methanol (90/10); 1H NMR spectrum (200 MHz, (CD3)2SO with addition of a few drops of CD3COOD, at a temperature of 373 K, δ in ppm): 1.53 (s, 9H: C(CH3)3); from 2.45 to 2.88 (2 mts, 1H each: CH2 at 3); 3.10 (s, 3H: SO2CH3); 3.70 and 4.02 (broad d and d respectively, J=17 Hz, 1H each: COCH2N); 3.96 (mt, 1H: H4); 4.67 (t, J=8 Hz, 1H: H2); 5.83 (d, J=3 Hz, 1H: H5); from 7.10 to 7.65 (mt, 6H: aromatic H); 7.92 (broad t, J=8 Hz, 1H: H of the aromatic at 5 (H6)); 7.98 (t, J=1.5 Hz, 1H: aromatic H (H2 ortho to the COOH))].

Provenance & Evidence