Ammonium formate → HCID 86751596, compound

Participants

Reaction Steps

The process is performed as in Example 4, but starting with 0.58 g of (2S,4S,5R)-3-{2-{3-[(S)-3-(1-benzyloxycarbonylethyl)phenyl]ureido}acetyl}-2-tert-butoxycarbonyl-4-phenyl-5-thiazolidinecarboxylic acid, 0.34 g of ammonium formate and 0.6 g of 10% palladium-on-charcoal. 0.21 g of 2-{3-{3-[2-((2S,4S,5R)-2-tert-butoxycarbonyl-5-carboxy-4-phenyl-3-thiazolidinyl)-2-oxoethyl]ureido}phenyl}propionic acid is thus obtained in the form of a white solid melting at 142° C., [α]D25 =+24.5°±0.6° (c=1.01; MeOH); 1H NMR (200 MHz, (CD3)2SO with addition of a few drops of CD3COOD, at a temperature of 373 K, δ in ppm): 1.41 (d, J=7 Hz, 3H: CH3); 1.51 (s, 9H: CH3 of the tert-butyl); 3.62 (q, J=7 Hz, 1H: CHCOO); 3.66 and 4.05 (broad d and d respectively, J=17.5 Hz, 1H each: COCH2 N); 4.18 (d, J=4 Hz, 1H: H at C5 of the ring); 5.72 (s, 1H: H at C2 of the ring); 5.77 (d, J=4 Hz, 1H: H at C4 of the ring); 6.86 (broad d, J=7.5 Hz, 1H: aromatic H (H ortho to the CH)); 7.17 (t, J=7.5 Hz, 1H: aromatic H (H meta to the CH); from 7.20 to 7.50 (mt, 5H: aromatic H); 7.73 (dd, J=7.5 and 1.5 Hz, 2H: H ortho to the phenyl).

Provenance & Evidence