Diisopropylcarbodiimide → HCID 178454157, compound

Participants

Reaction Steps

To a round bottomed flask was added N-(tert-butoxycarbonyl)-L-phenylalanine (109 mg) and dichloromethane (10 ml). To the solution was added diisopropylcarbodiimide (64 μl), trans-4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexanol (150 mg) and 4-dimethyl aminopyridine (catalytic). The solution was stirred at room temperature for 15 hr. The reaction mixture was partitioned between water (20 ml) and dichloromethane (30 ml), the layers were separated and the aqueous phase was extracted with dichloromethane (2×30 ml). The combined organic phases were washed with brine (20 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification via flash chromatography (SiO2, ethyl acetate/petroleum ether, 1:19 v/v) furnished the title compound (236 mg, 100%) as a yellow oil. δH (CDCl3): 0.18 (6H, s), 0.23 (6H, s), 0.97 (9H, s), 1.03 (9H, s), 1.35-1.47 (13H, m), 1.80-1.90 (2H, m), 1.95-2.07 (2H, m), 2.77-2.86 (1H, m), 3.05-3.12 (2H, m), 4.49-4.58 (1H, m), 4.73-4.82 (1H, m), 4.93-5.00 (1H, m), 6.28 (1H, d), 6.40 (1H, dd), 6.93 (1H, d), 7.15 (2H, d), 7.19-7.31 (3H, m).

Provenance & Evidence