Water ethanol → Sampatrilat

Participants

Reaction Steps

A solution of (S,S,S)-N-(1-[3-(N6-benzyloxycarbonyl-N2-mesyllysylamino)-2-carboxypropyl]-1-cyclopentylcarbonyl)tyrosine (see Preparation 9) (371 g) in a 9:1 ethanol/water mixture (2.225 l) was hydrogenated at 414 kPa (60 psi) and room temperature over a 10% palladium-on-carbon catalyst (37.0 g) for 4 hours. The catalyst was filtered off and the filtrate evaporated to leave the crude product as a foam. This material was stirred with acetone (3.13 l) for 24 hours to give the title compound as a white amorphous solid (283 g). Found: C,52.97; H,7.02; N,8.97. C26H40N4O9S requires: C,53.41; H,6.90; N,9.58%.

Provenance & Evidence