Water → HCID 57062129, compound

Participants

Reaction Steps

To a solution of 17-tetrabenzo(a,c,g,i)fluorenylmethyl-para-nitrophenyl carbonate (139.4 mg, 0.248 mmol) and L-phenylalanine tert-butyl ester acetate (83.9 mg, 0.298 mmol; 1.2 equiv) in dichloromethane (5 ml) was added N,N′-dimethylaniline (63 μl, 0.497 mmol; 2 equiv). The reaction mixture was stirred at room temperature under nitrogen for 120 h. After addition of water (10 ml) and acidification with KHSO4 (2M) to pH=1, the reaction mixture was extracted with dichloromethane (3×20 ml). The combined organic phases were washed with water (2×15 ml) to pH 6-7 and dried over MgSO4. After filtration the solvent was evaporated under reduced pressure to give an orange oil. After purification by flash chromatography using toluene as the eluent, the fractions containing material of Rf=0.04 were evaporated to give a yellow solid. Recrystallization from ether/petrol (b.p. 40-60° C.) gave compound (54) as a pale yellow solid which was filtered, washed with petrol and finally dried (73.9 mg, 46%);

Provenance & Evidence