Benzyl chloroformate → HCID 22614951, compound

Participants

Reaction Steps

To a solution of the compound in Example 40 (15 mg, 0.03 mmol) in anhydrous THF/H2O were added K2CO3 and benzyloxycarbonyl chloride (3 eq), the mixture was stirred for 3 hours. The crude mixture was purified over SiO2 column. The product was dissolved in anhydrous DMF (2 ml), NaH (5 mg) was added. The mixture was stirred for 10 minutes. Ethyl bromide (excess) was added to the reaction flask. The mixture was stirred for one hour. The crude product was hydrogenated over 10% Pd/C in MeOH to give the desired product as a colorless oil. ESI-MS: m/z 501 (MH+); 1H-NMR (CDCl3): δ 1.36 (3H, t, J=6.9 Hz), 2.16 (2H, m), 2.43 (3H, s), 2.98 (2H, t, J=6.9 Hz), 3.72 (2H, q, J=6.9 Hz), 3.94 (2H, s), 4.25 (2H, t, J=5.9 Hz), 4.68 (2H, s), 5.20 (2H, s), 5.40 (2H, s), 6.69 (1H, d, J=7.9 Hz), 6.73 (1H, s), 7.08 (1H, dd, J=9 Hz, 2.5 Hz), 7.18 (1H, d, J=18 Hz), 7.25-7.32 (3H, m), 7.46 (1H, d, J=9 Hz), 7.75 (1H, d, J=7.9 Hz), 8.59 (1H, dd, J=5 Hz, 1.5 Hz), 8.66 (1H, d, J=1.5 Hz).

Provenance & Evidence