[cis-2-[[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]methyl]-1-(4-methoxyphenyl)-4-oxo-3-azetidinyl]carbamic acid 1,1-dimethylethyl ester → [[[cis-3-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-oxo-2-azetidinyl]methoxy]imino]acetic acid

Participants

Reaction Steps

A solution of the oxyamine produced in Example 1 (637 mg, 2.75 mmol) and glyoxylic acid monohydrate (295 mg, 3.20 mmol) in THF (25 ml) was allowed to stir for 1 hour. The solvent was removed under reduced pressure and the resulting solid triturated with a solution of methanol-methylene chloride (1:20) to afford [[[cis-3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-oxo-2-azetidinyl]methoxy]imino]acetic acid (630 mg, 79%): IR (KBr) 3325, 2960, 1755, 1705, 1685, 1595, 1515, 1330, 1265, and 1155 cm-1 ; NMR (DMSO-d6) δ 1.40 (9H, s), 3.86 (1H, m), 4.25 (2H, m), 4.88 (1H, dd, J=9, 5 Hz), 7.59 (1H, s), 7.65 (1H, d, J=9 Hz, exchangeable), 8.40 (1H, s, exchangeable); FAB HRMS, m/e 288.1194 (M+ calculated for C11H18O6N3 : 288.1195).

Provenance & Evidence