Triethylamine → HCID 54518839, compound

Participants

Reaction Conditions

Reaction Steps

p-Methoxybenzyl glyoxylate (3.20 g, 16.5 mmol) in 1,2-dichloroethane (50 ml) was heated at reflux for 1h. using Dean and Stark apparatus. The solution was cooled in ice and treated successively with (3S,4R)-4-[3-oxo-3-[(S)-tetrahydrofuran-2-yl]propyl]-3-phenylacetamidoazetidin-2-one (4.10 g, 12.4 mmol) and triethylamine (170 μl, 1.22 mmol). After stirring at 0° C. for 30 min., the reaction mixture was concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with 50% ethyl acetate in hexane, then ethyl acetate to yield the title compound as a yellow foam (4.53 g, 70%); νmax (CH2Cl2) 3420, 3226, 1769, 1743, 1681, 1613 and 1516 cm-1 ; m/z (FAB, +ve ion, 3-nitrobenzyl alcohol/sodium acetate) 547 (MNa+).

Provenance & Evidence