HCID 59784092, compound → HCID 59784098, compound

Participants

Reaction Steps

Compound 6 (13.02 g, 19.2 mmol) is dissolved in MeOH (600 mL), to which is added 5% Pd/C (1.80 g). This mixture is stirred in a pressure vessel under an atmosphere of hydrogen (40 psi) for 2 h. The catalyst is then removed by filtration over celite and the solvent removed from the resulting filtrate to afford a crude oil which is purified by flash chromatography on silica gel (5% MeOH/CH2Cl2). The desired product 7 is obtained as a white foam (9.71 g, 93% yield): 1H NMR δ (CDCl3) 7.02-7.20 (m, 4H), 6.71 (br s, 1H), 6.37 (br d, J=8.8 Hz, 1H), 4.16-5.13 (br m, 4H), 3.10-3.71 (br m, 3H), 2.64-2.84 (br m, 7H), 1.58-2.11 (br m, 7H), 1.46 (s, 9H), 1.30 (d, J=7.1 Hz, 2H), 0.86-1.02 (br m, 3H), 0.75 (d, J=6.7 Hz, 2H), 0.53 (br d, J=6.7 Hz, 2H); LCMS (APCl+) 544.9 (MH+), 444.6 (MH+-BOC), 260.2 (MH+-dipeptide, 100%); HPLC (C8 column) 95.2%.

Provenance & Evidence