Sodium Hydroxide → HCID 10257209, compound

Participants

Reaction Steps

2-[3-Benzyloxycarbonylamino-2-oxo-5-(4-pivaloyloxybenzyl)-1,2-dihydro-1-pyridyl]-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl]acetamide was dissolved in methanol and excess 2N sodium hydroxide was added. The mixture was allowed to stir for 3 h, was evaporated, and partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was washed (brine), dried, evaporated and purified by chromatography, using dichloromethane:methanol (gradient, 99:1, 95:5) as the eluent, to give the title compound; NMR: 0.78-0.91 (m,6), 2.20 (m,1), 4.09 (m, NHCH hydrate), 4.50-4.77 (m,3, CH2CO, NHCH keto), 5.13 (s,2), 6.68 (d,2, J=8), 6.95 (m, OH hydrate), 6.96 (d,2, J=8), 7.20 (m,1) 7.29-7.42 (m,5), 7.70 (m,1), 7.73 (d, J=10), 8.33 (s, NH hydrate), 8.37 (S, NH keto), 8.93 (d, J=6.5, NH keto), 9.24 (s,1, OH).

Provenance & Evidence