Trifluoroacetic acid → HCID 178449772, compound

Participants

Reaction Steps

To a solution of 2-(3-(N,N′-di(t-butoxycarbonyl)guanidino)phenyl)-2-((1-(benzyloxycarbonyl)amino-2-methylpropyl)(hydroxy)phosphinoyloxy)ethanoic acid in 10 mL of CH2Cl2 was added 5 mL of TFA. After stirring for 2 hours at ambient temperature, the solution was concentrated in vacuo and azeotrope with CH2Cl2 and MeOH. Purification by preparatory HPLC separated the two diastereomers and provided 72.9 mg (8%) of one diastereomer and 90.1 mg (10%) of 2-(3-guanidinophenyl)-2-((1-(benzyloxycarbonyl)amino-2-methylpropyl)(hydroxy)-phosphinoyloxy)ethanoic acid, NMR (DMSO-d6) 0.85 (m, 6), 2.05 (m, 1), 3.70 (m, 1), 4.80 (AB q, 2: doublets at 4.70, 4.90), 5.65 (d, 1), 7.20 (d, 1), 7.25-7.50 (m, 14), 9.85 (s, 1) ppm.

Provenance & Evidence