(S)-benzyl 4-(tert-butoxycarbonylamino)-5-((R)-1-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-ylamino)-1-oxo-4-(4-(trifluoromethyl)phenyl)butan-2-ylamino)-5-oxopentanoate → (S)-4-(tert-butoxycarbonylamino)-5-((R)-1-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-ylamino)-1-oxo-4-(4-(trifluoromethyl)phenyl)butan-2-ylamino)-5-oxopentanoic acid

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Reaction Steps

To a solution of (S)-benzyl 4-(tert-butoxycarbonylamino)-5-((R)-1-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-ylamino)-1-oxo-4-(4-(trifluoromethyl)phenyl)butan-2-ylamino)-5-oxopentanoate (1.8 g, 2.48 mmol) in a mixture of EtOH/H2O (20 mL/2 mL) was added Pd(OH)2/C (cat.). The mixture was stirred under a H2 atmosphere for 2 h. The mixture was filtered through Celite and washed with MeOH. The filtrate was evaporated to dryness under vacuum to produce (S)-4-(tert-butoxycarbonylamino)-5-((R)-1-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-ylamino)-1-oxo-4-(4-(trifluoromethyl)phenyl)butan-2-ylamino)-5-oxopentanoic acid (CLXXI) as a white foam (1.57 g, 2.48 mmol, 100% yield). ESIMS found for C30H37BF3N3O3 m/z 634.6 (M−H).

Provenance & Evidence