(3R)-N-(benzyloxy)-6-cyclohexyl-3-{4-[(isopropylamino)methyl]-1,3-oxazol-2-yl}hexanamide → (3R)-6-cyclohexyl-N-hydroxy-3-{4-[(isopropylamino)methyl]-1,3-oxazol-2-yl}hexanamide

Participants

Reaction Conditions

Reaction Steps

A solution of (3R)-N-(benzyloxy)-6-cyclohexyl-3-{4-[(isopropylamino)methyl]-1,3-oxazol-2-yl}hexanamide (preparation 157) (85 mg, 0.20 mmol) in EtOH (5 ml) was treated with HCO2NH4 (63 mg, 1.00 mmol) and Pd(OH)2 (20 mg) and the reaction mixture heated at 43° C. for 18 hours. 2 further portions of HCO2NH4 (30 mg+30 mg) and Pd(OH)2 (10 mg+30 mg) were added over a period of 4 hours. The catalyst was filtered off and washed with EtOH. The solvent was removed under reduced pressure. The crude material was purified on a silica column eluting with DCM:MeOH:NH3 (90:10:1) to afford the title compound.

Provenance & Evidence