Acetic Acid → HCID 86747603, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of allyl (5R,6S)-3-[2-allyloxycarbonylamino-1-(N-allyloxycarbonylaminomethyl)ethyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (858 mg) in tetrahydrofuran (12 ml) and ethanol (4 ml) were added successively triphenylphosphine (0.19 g), acetic acid (0.10 ml) and tetrakis(triphenylphosphine)palladium (0.16 g) at room temperature under nitrogen. The temperature was raised to 30° C. and after all components were dissolved, tributyltin hydride (1.94 ml) was added dropwise. After stirring for 15 minutes at room temperature, ethyl acetate (50 ml) was added. After 30 minutes, the precipitate was filtrated and washed with ethyl acetate and dichloromethane under nitrogen, and dissolved in buffer solution (68 ml, pH 6.86). Ethyl 2-ethoxycarbonylacetoimidate hydrochloride (599 mg) was added to the solution at pH 8.5. After stirring for 30 minutes at pH 8.5. The mixture was stirred for 30 minutes at pH 7. After the starting material disappeared, the reaction mixture was washed five times with ethyl acetate-tetrahydrofuran (7:3, V/V, 70 ml) at pH 7. The aqueous layer was evaporated and the residue was purified by Diaion HP-20 column chromatography (eluent:acetonitrile-water=4:96, V/V) and silica gel column chlomatorgaphy (eluent:acetonitrile-water=100:00-85:15, V/V) to give (5R,6S)-6-[1R)-1-hydroxyethyl]-3-[2-(ethoxycarbonylmethyl)-3,4,5,6-tetrahydropyrimidin-5-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (56.4 mg).

Provenance & Evidence