Sodium Hydroxide → (7R)-7-[{2-[(tert-butoxycarbonyl)amino]ethyl}(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

2N NaOH (aq) (6 eq) was added to a solution of methyl (7R)-7-[{2-[(tert-butoxycarbonyl)amino]ethyl}(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.02 M) in MeOH/THF (3/1) and the reaction stirred vigorously at 60° C. for 4 h. The reaction was allowed to cool to RT before reducing the volume of MeOH/THF in vacuo. The residue was partitioned between 1N HCl (aq) and EtOAc, ensuring the aqueous phase was acidic. The aqueous was extracted a second time with EtOAc and the combined organics washed with water, brine before being dried (Na2SO4), filtered and concentrated in vacuo. The material was taken on without further purification. MS (ES+) m/z 548 (M+H)+.

Provenance & Evidence