Lithium Hydroxide → HCID 178449993, compound

Participants

Reaction Steps

To a solution of 2-(3-(N′,N″-di(t-butoxycarbonyl)guanidino)phenyl)-2-((1-(2-phenylethenylsulfonyl)amino-2-methylpropyl)(hydroxy)-phosphinoyloxy)ethanoic acid, methyl ester (220 mg) in 5 mL methylene chloride was added 1 mL TFA. The reaction mixture was stirred at ambient temperature for 4 hours, then concentrated in vacuo to get an oil. The oil was dissolved in 2.5 mL MeOH, then a solution of LiOH (100 mg) in 3 mL water was added. The reaction mixture was stirred at ambient temperature for 2 hours. The crude product was purified by HPLC directly without work up to afford 2-(3-guanidinophenyl)-2-((1-(2-phenyl-ethenylsulfonyl)amino-2-methylpropyl)-(hydroxy)phosphinoyloxy)ethanoic acid, as a white solid (55 mg) NMR (DMSO-d6) 0.88 (m,6), 2.10 (m,1), 3.40 (m,1), 5.63 (m, 1), 7.10-7.60 (m, 11), 9.80 (d, 1) ppm.

Provenance & Evidence