Sodium Bicarbonate → HCID 13422902, compound

Participants

Reaction Steps

181 mg (0.96 mmol--1.2 equivalents) of anhydrous tin-II chloride (dried by fusing briefly under a high vacuum) were added all at once, at 0° C., to a suspension of 150 mg (0.78 mmol) of (1R, 5S)-3-phenyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-7-one in 1.3 ml of anhydrous methlene chloride and 0.81 ml (7.8 mmols--10 equivalents) of 3-methyl-2-buten-1-ol. The cooling bath was removed and a clear solution was formed after a few minutes. The reaction mixture was stirred for a further 15 minutes at room temperature, poured into dilute NaHCO3 solution and extracted with methylene chloride and the extract was washed with water and dried over MgSO4. After the solvent had been evaporated off in vacuo and the residue had been filtered on 5 g silica gel (toluene:ethyl acetate 3:7), 153 mg (70%) of the title compound were obtained as colorless crystals, melting point: 92° C., RF : 0.38 (toluene:ethyl acetate 3:7).

Provenance & Evidence