Methanol → HCID 178476726, compound

Participants

Reaction Steps

1.0 g of benzyloxycarbonyl-L-histidyl-L-prolyl-β-alaninamide were dissolved in 50 ml of methanol and hydrogenated with the addition of palladium/carbon. The catalyst was filtered off and the filtrate concentrated in vacuo. The residue was dissolved in 10 ml of dimethylformamide and treated with 0.9 g of L-pyroglutamic acid pentachlorophenyl ester. The mixture was stored for 24 hours at room temperature and then concentrated in vacuo. The residue was dissolved in water and chromatographed on a Dowex 2 column (OH form). The fractions which were uniform in a thin-layer chromatogram were combined, acidified with acetic acid and lyophilised. Yield: 0.8 g. [α]D25 = -82.2° (c = 1 in 1 N acetic acid).

Provenance & Evidence