Réaction #1833259

Équation de réaction

water

β-lactam

3-Acetoxy-N-(4-methoxyphenyl)-4-(2-chlorophenyl)-2-azetidinone

KOH

→

24

Rendement 96.9%

3-Hydroxy-N-(4-methoxyphenyl)-4-(2-chloro phenyl)-2-azetidinone

Rendement 96.9%

Solvants

acetone

methanol

Conditions de réaction

Traitement

1. 1
   AutreThe product was precipitated
2. 2
   Autreisolated by filtration

Mode opératoire

To a solution of β-lactam 23 (8.00 g, 23.1 mmol) in 50 ml of acetone was added KOH (1.30 g, 23.1 mmol) in 20 ml of methanol at 0° C. The resultant mixture was stirred for 5 minutes, and 50 ml of water was added. The product was precipitated and isolated by filtration to yield 6.8 g (96%) of 24 as a white solid, mp 178-180° C. 1H NMR (250 MHz) δ 7.48 (d, J=7.3 Hz, 1H), 7.34-7.24 (m, 5H), 6.85 (d, J=9.0 Hz, 2H), 5.63 (d, J=5.1 Hz, 1H), 5.34 (d, J=5.1 Hz, 1H), 3.78 (s, 3H), 1.74 (bs, 1H). 13C NMR (63 MHz, DMSO-d6), δ 166.6, 156.1, 133.1, 132.9, 131.0, 129.8, 129.6, 128.9, 127.4, 118.6, 115.0, 77.2, 60.0, 55.7.

Source