Pyridine → [[[[cis-3-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-oxo-2-azetidinyl]methoxy]amino]sulfonyl]acetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of the oxyamine produced in Example 1 (495 mg, 2.1 mmol) in dry THF containing pyridine (1.1 eq.) was added ClSO2CH2CO2CH3 and the solution was stirred for 1 hour at 0° C. The reaction mixture was diluted with ethyl acetate and washed with 1N HCl, 5% sodium bicarbonate, brine and dried over anhydrous magnesium sulfate. The product was purified by flash chromatography (ethyl acetate-hexane, 1:2) to afford 426 mg (54%) of [[[[cis-3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-oxo-2-azetidinyl]methoxy]amino]sulfonyl]acetic acid methyl ester: mp 128°-129° C. (CH2Cl2); IR (KBr) 3340, 3210, 2975, 1780, 1740, 1685, 1525, and 1160 cm-1 ; NMR (DMSO-d6) δ 1.40 (9H, s), 3.75 (3H, s), 3.90 (1H, m), 4.00 (2H, m), 4.34 (1H, d, J=15 Hz), 4.42 (1H, d, J=15 Hz), 4.94 (1H, d, J=9, 6 Hz), 7.68 (1H, d, J=9 Hz, exchangeable), 8.44 (1H, s, exchangeable).

Provenance & Evidence