Nitrogen → HCID 86736766, compound

Participants

Reaction Steps

To a solution of 2-methoxyethoxythioacetic acid (990 mg.; 6.60 mmoles) in 1N KOH (6.0 ml.) and water (30 ml.) was added in an ice-bath under nitrogen atmosphere 4-acetoxy-2-azetidinone (777 mg.; 6.00 mmoles). The reaction mixture was stirred at room temperature (N2) for 1 hr. and then extracted with methylene chloride (30 ml.×3). The extracts were washed with brine, dried (Na2SO4) and evaporated yielding 4-(2-methoxyethoxythioacetoxy)-2-azetidinone (1.26 g.; 5.76 mmoles; 96% yield) as a yellow oil. nmr (CDCl3): δppm 2.8-3.8 (2H, m, H-3), 3.40 (3H, s, -OCH3), 3.4-3.9 (4H, m, -CH2CH2 -O), 4.25 (2H, s, O=CCH2O-), 5.25 (1H, dd, J3-4 cis =5 Hz, J3-4 trans =3 Hz, H-4), 7.3 (1H, br.s, -NH); ir (neat): 3280 cm-1 (νN-H), 1770 (νc=o, β-lactam), 1690 (νc=o, thioester).

Provenance & Evidence