Dimethylformamide → Boc-Ala-Ala-OMe

Participants

Reaction Conditions

Reaction Steps

To a cold (−15° C.) solution of Boc-Ala-OH (1.034 g, 5.47 mmol) and NMM (901 μl, 8.20 mmol) in THF (15 mL) was added ECF (538 μl, 5.63 mmol) under N2 atmosphere and vigorously stirred. After 2 min of stirring, a solution of methyl alaninate hydrochloride (840 mg, 6.01 mmol) in a mixture of solvents THF:DMF (4 mL:3 mL) was added to the reaction mixture followed by NMM (1.5 mL, 13.67 mmol) and stirred. After 10 min the mixture was warmed to 25° C. and stirred for further 8 h. THF was removed under reduced pressure and the resulting viscous solution was diluted with water (10 mL) and thoroughly extracted with ethyl acetate. The combined organic extracts were washed with saturated citric acid (10 mL), saturated NaHCO3 (10 mL) and dried over by Na2SO4 and concentrated under reduced pressure to give a residue, which was purified by silica gel flash column chromatograph (EtOAc:Hexane—3:17) to give the desired product as a solid (m.p. 107-108° C.) in good yields (1.48 g, 98.6%). (TLC:EtOAc:Hexanes 7:3—Rf—0.55).

Provenance & Evidence