Ammonium formate → HCID 57815105, compound

Participants

Reaction Steps

To a 0.5 ml solution of benzyl 2-amino-4-(2-methoxyethyl)-1H-imidazole-1-carboxylate prepared in a similar manner to Example 32 63 mg (0.22 mmol), (2R,3S)-2-hydroxy-3-{[3-[methyl(methylsulfonyl)amino]-5-({[(1R)-1-phenylethyl]amino}carbonyl)benzoyl]amino}-4-phenylbutanoic acid obtained in Reference Example 39 63 mg (0.11 mmol) and HOBt —H2O 18 mg (0.12 mmol) in DMF was added EDC.HCl 23 mg (0.12 mmol) under ice-cooling and the mixture was heated to room temperature and stirred for 2 hours. The reaction solution then was extracted by adding ethyl acetate and 5% aqueous sodium carbonate solution. The organic layer was washed with an aqueous saturated sodium chloride solution and dried on sodium sulfate. Filtration and concentration gave a residue and the resulting residue was redissolved in methanol 2 ml and thereto were added ammonium formate 126 mg (2.00 mmol) and 10% Pd/C (containing 50%) 50 mg and the mixture was heated under reflux for 1.5 hours. The mixture was filtered to remove 10% Pd/C and concentrated. The concentrated residue was suspended in ethyl acetate and the mixture was washed with 5% sodium carbonate and an aqueous saturated sodium chloride solution. The organic layer was dried on sodium sulfate. After filtration and concentration of the mixture, the mixture was purified by a column chromatography on silica gel (eluted with a mixed solvent of chloroform and methanol) to give 50 mg (0.07 mmol) of the title compound (yield: 67%).

Provenance & Evidence