Water → HCID 70268268, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl (-)-[S-(R*,R*)]-3-[[[[2-[[[[(4-methylphenyl)sulfonyl]amino]carbonyl]-amino]-1,2-diphenylethyl]amino]carbonyl]amino]benzoate (0.1 g, 0.17 mmol), in MeOH (5 mL) is added lithium hydroxide monohydrate (0.006 g, 0.17 mmol) followed by water to the cloud point. The resulting mixture is warmed to 50° C. for 4 hours. The solvent is removed in vacuo and the residue partitioned between water and diethyl ether. The layers are separated and the aqueous layer is acidified to pH=2 with 2 M HCl. The resulting solid is filtered and dried in vacuo at 114° C. for 5 hours, mp 185°-189° C. IR (KBr): 3383, 1699, 1558, 699 cm-1. NMR (DMSO-d6): δ2.31 (s, 3H), 4.87-5.04 (m, 2H), 6.84-7.72 (m, 19H), 8.07 (s, 1H), 8.77 (s, 1H), 10.65 (br s, 1H), 12.87 (br s, 1H). Analysis calculated for C30H28N4O6S.1.63H2O: C, 59.86; H, 5.23; N, 9.31. Found: C, 59.85; H, 4.96; N, 9.35. [α]D25 =-3.7° (c=1, DMF).

Provenance & Evidence