Dichloromethane → HCID 86737254, compound

Participants

Reaction Steps

Benzhydryl (2-oxo3-azido-4-[3-keto-4-hydroxybutyl]-N-azetidinyl)diethylphosphonoacetate, 251 mg., is treated at 0° under N2 in 22 ml. CH2Cl2 with 0.056 ml. methanesulfonyl chloride for 5 min., and then .100 ml. triethylamine is added. After 2 min. more at 0° and 30 min. at 25°, the solvent is evaporated and the product chromatographed by PLC, eluting with 10:3 CHCl3 -acetone, affording 197 mg. pure benzyhydryl (2-oxo-3-azido-4-[3-keto-4-methanesulfonyloxybutyl]-N-azetidinyl)diethylphosphonoacetate. NMR (δ, CDCl3): 1.24 m, POCH2CH3 ; 2.0-2.5 m, CH2CH2 ; 3.14 s, CH3SO2 ; 3.8-4.4 m, POCH2CH3 ; 4.71 s, COCH2OSO2Me; 5.09 d, J=22, CHP; 6.93 s, CHφ2 ; 7.36 s, Ar. IR (μ, film): 4.73, azido; 5.64, β-lactam; 5.72, ester.

Provenance & Evidence