Dicyclohexylcarbodiimide → HCID 86603903, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of ethyl N-hydroxyacetimidate 1 (6.2 g, 60 mmol) and 8-bromooctanoic acid (15 g, 67 mmol) in 150 mL of solvent mixture (methanol 8: acetone 1) was added drop wise 22 mL of 10N NaOH and heated at 50° C. for 12 h. The reaction mixture was cooled, the organic solvent was removed by rotary evaporation. The dilute HCl solution was added to adjust pH down to 6. The resulting turbid mixture was extracted with CHCl3 and EtOAc. The extract was washed with brine, dried, filtered, and solvent was evaporated to crude oil (3, 12 g, 49 mmol, 82%). A mixture of 3 (12 g, 49 mmol) and N-hydroxysuccinimide (5 g, 50 mmol) in 100 mL of THF was treated with 50 mL of DCC (1.0 M solution in CH2Cl2). The solids were filtered, and the clear filtrate was evaporated. The resultant brown oil was purified on a silica gel column. Elution with 20% ethyl acetate/hexane afforded 5.8 g (17 mmol, 34%) of the product as a wet solid. 1H NMR (DMSO-d6): δ 1.21 (3H, t, J=7.0), 1.28-1.38 (6H, m), 1.57 (2H, p, J=6.8), 1.64 (2H, p, J=7.4), 1.86 (3H, s), 2.65 (2H, t, J=7.5), 2.81 (4H, s), 3.82 (2H, t, J=6.5), 3.94 (2H, q, J=7.0)

Provenance & Evidence