HCID 67074477, compound → HCID 67074020, compound

Participants

Reaction Steps

63.1 g (0.13 mol) of 3-{{(R)-2-[tert-butoxycarbonyl-(3-hydroxy-propyl)-amino]-1-methyl-ethyl}-[(E)-3-(3-chloro-phenyl)-acryloyl]-amino}-propionic acid methyl ester was dissolved in 130 ml of 4 N HCl in MeOH. The reaction was stirred for 4 h after which time it was evaporated to dryness and the residue redissolved in CH2Cl2, washed with sat. aq. NaHCO3, dried (Na2SO4) and the mixture concentrated to 300 ml. 3.6 g (0.03 mol) of 1,5,7-triazabucyclodec-5-ene was then added and the mixture stirred for 16 h after which time the solvent was evaporated. The residue was redissolved in 100 ml of MeOH and 6N NaOH was added until the pH was basic and the mixture stirred for 1 h. The solvent was evaporated, the residue redissolved in CH2Cl2, washed with 10% citric acid solution, washed with sat. aq. NaHCO3, dried (Na2SO4) and concentrated. This afforded the titled compound in 62% yield as a colorless foam. MS: 351.2 (MH+, Cl).

Provenance & Evidence