Thionyl Chloride → HCID 20347463, compound

Participants

Reaction Steps

To 800 mg. of p-nitrobenzyl 2-[4-(2-methoxyethoxyacetylthio)-2-oxo-1-azetidinyl]-2-hydroxyacetate was added (all at once) at 0° under N2 atmosphere, thionyl chloride (3 ml.) and the mixture was stirred at room temperature under N2 for 1 hour. The excess of thionyl chloride was removed in vacuo and the residue dissolved in dry benzene (10 ml.) and evaporated to dryness. There was obtained the title product (791 mg.) as a yellowish oil. nmr (CDCl3): δppm 2.9-3.9 (2H, m, H-3), 4.10 (3H, s, --OCH3), 3.5-3.9 (4H, m, --OCH2CH2O--), 4.24 (2H, s, O=C--CH2O--), 5.35-5.45 (2H, m, --CH2 --Ar), 5.70 (1H, m, H-4), 6.12 (1H, s, --CHCl), 7.52, 7.67, 8.21, 5.39 (4H, A2 ' B2 ', aromatic --H); ir (neat): 1780 cm-1 (broad, γc=o, β-lactam and ester), 1695 (γc=o, thioester), 1525 (γNO2).

Provenance & Evidence