Sodium Hydroxide → HCID 18791670, compound

Participants

Reaction Steps

To a mixture of 4-[2-[(3-tert-butoxycarbonylaminoprop-1-yl)oxy]benzoyl]amino-3-methoxy-N-methyl-N-[2-[5-(4-oxopiperidin-1-yl)carbonylpent-1-yl]oxy-4-methylphenyl]benzamide (250 mg), ammonium acetate (51 mg) and acetic acid (0.5 ml) in methanol (10 ml) was added sodium cyanoborohydride (21 mg) at 0° C. and the mixture was stirred at ambient temperature for 12 hours. The mixture was poured into ice-cooled 1N aqueous sodium hydroxide solution (15 ml) and the solution was extracted with chloroform (15 ml×3). The organic layer was washed with brine and dried over potassium carbonate. The solvent was evaporated in vacuo and the residue was purified by silica gel column chromatography (SiO2 40 g, 5-15% methanol in chloroform) to give 4-[2-[(3-tert-butoxycarbonylaminoprop-1-yl)oxy]benzoyl]amino-3-methoxy-N-methyl-N-[2-[5-(4-aminopiperidin-1-yl)carbonylpent-1-yl]oxy-4-methylphenyl]benzamide (91 mg).

Provenance & Evidence