Ammonium formate → HCID 67342806, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(tert-butoxycarbonyl)-2,6-dimethyl-L-tyrosyl-N-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-phenylpropyl]-D-alaninamide (450 mg, 0.70 mmol) from preparation 2 in methanol (10 mL) was added palladium hydroxide (40 mg) and ammonium formate (231 mg, 3.48 mmol) at room temperature. The reaction was then heated at 60° C. for 3 hours, after this time the reaction was allowed to cool and then filtered through a pad of Arbocel. The filtrate was concentrated under reduced pressure, the residue dissolved in methanol (5 mL) and loaded onto a 20 g SCX2 cartridge (pre-wetted with methanol). The cartridge was eluted with methanol to remove non-basic impurities and then eluted with 3M NH3 in methanol. Fractions containing the title compound were combined and concentrated under reduced pressure to afford the title compound as a white amorphous solid in 95% yield, 338 mg. 1H NMR (400 MHz, MeOH-d4) δ : 1.09 (d, 3H), 1.36 (s, 9H), 2.23 (s, 6H), 2.51-2.61 (m, 1H), 2.72-2.89 (m, 2H), 3.01-3.28 (m, 4H), 3.96-4.06 (m, 1H), 4.14-4.28 (m, 2H), 6.46 (s, 2H), 7.11-7.35 (m, 5H).

Provenance & Evidence