Water → 4-(2-Chlorophenyl)-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one

HRID 1746077Notes

Reaction equation

HRID 1746077 reaction equation
C([O:4][CH:5]1[CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[N:7]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:6]1=[O:24])(=O)C.[OH-].[K+].O>CC(C)=O.CO>[OH:4][CH:5]1[CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[N:7]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:6]1=[O:24]

Participants

6

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 69445558HCID 69445558, compound

Product 1

HCID 694464424-(2-Chlorophenyl)-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-oneYield 96.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

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.

Workup

  1. customThe product was precipitated
  2. customisolated by filtration

Sources & evidence

ORD record
ord-e6a0f7f980de4a7e82857c08b77352ab
Source dataset
uspto-grants-2015_10
Patent number
US09149440B2

Reaction notes

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