Potassium Carbonate → HCID 54471702, compound

HRID 842750Notes

Reaction equation

HRID 842750 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][CH3:19])=[O:17].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:19][O:18][C:16](=[O:17])[CH2:15][O:1][C:2]1[CH:13]=[CH:12][CH:11]=[C:4]([CH2:5][NH:6][S:7]([CH3:10])(=[O:9])=[O:8])[CH:3]=1

Participants

5

Reactant 3

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

Product 1

HCID 54471702HCID 54471702, compound

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 of Preparation 10 (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)
  4. customprovided

Sources & evidence

ORD record
ord-1f551572c2ef4204be4e28f32f6e1387
Source dataset
uspto-grants-2002_04
Patent number
US06376502B1

Reaction notes

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