1,4-Cyclohexadiene → HCID 44409723, compound

Participants

Reaction Steps

2-{[bis(benzyloxy)phosphoryl]oxy}ethyl (1S)-1-{[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]carbonyl}-2,2-dimethylpropylcarbamate (9-2, 11 mg, 0.015 mmol, 1 equiv), 1,4-cyclohexadiene (1 mL, excess) and 10% Pd/C (5 mg) were added to methanol (4 mL) and the mixture was stirred under a nitrogen atmosphere. After 30 minutes another 5 mg of 10% Pd/C was added and stirring was continued for an additional hour. The reaction was filtered and the filtrate concentrated. The residue was purified by reverse phase LC (H2O/CH3CN gradient w/0.1% TFA present) to give 2-(phosphonooxy)ethyl (1S)-1-{[(2S)-4-2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]carbonyl}-2,2-dimethylpropylcarbamate (9-3) as a colorless foam. 1H NMR (500 MHz, CDCl3) major rotamer: δ 7.34-7.20 (m, 5H), 7.12-6.92 (m, 3H), 6.38 (s, 1H), 5.93 (bs, 1H), 5.21 (d, 1H, J=14 Hz), 4.91 (d, 1H, J=14 Hz), 4.41 (d, 1H, J=10 Hz), 4.38-3.97 (m, 7H), 0.91 (s, 9H). LRMS m/z (M+H) 539.5 found, 538.2 required.

Provenance & Evidence