Hydrochloric Acid → 1-{(2S,3S)-3-[N2-(4-Aminophenoxyacetyl)-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-L-prolinamide hydrochloride

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Reaction Steps

0.16 ml (0.16 mmol) of 1N aqueous hydrochloric acid was added to a solution of 105 mg (0.14 mmol) of 1-[(2S,3S)-3-{N2 -[4-(benzyloxycarbonylamino)phenoxyacetyl]-L-asparaginyl}amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-L-prolinamide (prepared as described in Example 16) in 5 ml of methanol, and the mixture was stirred for 2.5 hours in the presence of 70 mg of palladium on charcoal and under an atmosphere of hydrogen. At the end of this time, the catalyst was removed by filtration, and then the solvent was removed by distillation under reduced pressure. The resulting residue was mixed with benzene and the mixture was dehydrated by azeotropic distillation. This operation was repeated a second time, and then the residue was triturated with diethyl ether, to give 89 mg of the title compound as a red-brown powder, melting at 165°-168° C.

Provenance & Evidence