Potassium Carbonate → HCID 22246971, compound

HRID 890766Notes

Reaction equation

HRID 890766 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[CH2:5][NH:6][S:7]([CH3:10])(=[O:9])=[O:8].Br[CH2:15][C:16]([O:18]C)=[O:17].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:10][S:7]([NH:6][CH2:5][C:4]1[CH:3]=[C:2]([CH:13]=[CH:12][CH:11]=1)[O:1][CH2:15][C:16]([OH:18])=[O:17])(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 22246779HCID 22246779, compound

Product 1

HCID 22246971HCID 22246971, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of N-(3-hydroxy-benzyl)-methanesulfonamide (6.000 g, 29.82 mmol), methyl bromoacetate (4.562 g, 29.82 mmol), K2CO3 (4.121 g, 29.82 mmol), and acetone (250 mL) was stirred at room temperature for 68 h. The solids were removed by filtration and the solution was concentrated in vacuo. Purification by flash chromatography (1:1 hexanes:EtOAc) provided the title compound (5.637 g). 1H NMR (400 MHz, CDCl3) δ 7.25 (m, 1H), 6.96 (m, 1H), 6.89 (s, 1H), 6.82 (m, 1H), 4.63 (m, 3H), 4.28 (m, 2H), 3.80 (s, 3H), 2.86 (s, 3H); MS 274 (M+1).

Workup

  1. customThe solids were removed by filtration
  2. concentrationthe solution was concentrated in vacuo
  3. customPurification by flash chromatography (1:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-9910af22c90e40fd977f057a8559f166
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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