Ethyl diazoacetate → 2-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-cyclopropanecarboxylic Acid Ethyl Ester

Participants

Reaction Steps

To a solution of 5-(2-benzyloxy-4-vinylphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (Example 81, step A) (75 mg, 0.17 mmol) in methylene chloride is added rhodium acetate dimer (cat.). Ethyl diazoacetate (0.024 mL, 0.17 mmol) in methylene chloride (0.2 mL) is added dropwise via syringe pump over 4 h. The solvent is removed under reduced pressure and the crude material purified on silica gel using a gradient of 0-40% EtOAc/hexanes to give the title compound as a mixture of isomers (cis:trans 1:2) as a colorless oil: (M+H)+=548.

Provenance & Evidence