Sodium Bicarbonate → HCID 13422897, compound

Participants

Reaction Steps

10 μl of boron trifuloride etherate were sprayed into a stirred suspension of 376 mg (2mmols) of (1R, 5S)-3-phenyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-7-one and 941 mg (4 mmols) of 4-nitrobenzyl 4-hydroxy-2-butinoate in 8 ml of anhydrous tetrahydrofuran at room temperature. After a short time, a clear, light yellow solution formed, and was stirred at room temperature for 0.5 hour. Thereafter, the solution was poured into dilute NaHCO3 solution, the mixture was 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 chromatographed on 60 g of silica gel (toluene:ethyl acetate 35:65), 557 mg (66%) of 4-nitrobenzyl 4-[3(R)-benzoylamino-2-azetidinon-4(R)-yloxy]-2-butinoate were obtained as a colorless rigid foam.

Provenance & Evidence