Dicyclohexylcarbodiimide → 8-{[(Benzyloxy)carbonyl]amino}-1,2,3,4-tetrahydronaphthalen-2-yl (2r)-methoxy(phenyl)acetate

Participants

Reaction Steps

A mixture of Example 24B (1.03 g, 3.46 mmol), (R)-2-methoxy-2-phenylacetic acid (0.633 g, 3.81 mmol), 1,3-dicyclohexylcarbodiimide (1.14 g, 5.54 mmol), and 4-dimethylaminopyridine (0.846 g, 6.93 mmol) in dichloromethane (35 mL) was stirred at ambient temperature for 18 hr. The reaction mixture was diluted with CH2Cl2 and washed with saturated aqueous NH4Cl solution, brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was placed on a silica gel column and eluted with 30% ethyl acetate/hexanes to afford 1.38 g (89% yield) of the title compound as a colorless syrup. MS (ESI+) m/z 446 (M+H)+, 463 (M+NH4).

Provenance & Evidence