Methanesulfonyl chloride → HCID 59478663, compound

HRID 450792Notes

Reaction equation

HRID 450792 reaction equation
[NH2:1][C:2](=O)[CH2:3][C:4]1[CH:5]=[C:6]([CH2:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1.CS(Cl)(=O)=O>N1C=CC=CC=1>[C:2]([CH2:3][C:4]1[CH:5]=[C:6]([CH2:10][C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1)#[N:1]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86711697HCID 86711697, compound

Product 1

HCID 59478663HCID 59478663, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.31 g of 4-methoxybenzyl [3-(2-amino-2-oxoethyl)phenyl]acetate in pyridine (20 mL) was added 718 mg of methane sulfonyl chloride under ice-cooling, followed by stirring for 2 hours. The reaction solution was concentrated under reduced pressure. The residue was diluted with ethyl acetate and washed with a 5% aqueous citric acid solution, a saturated aqueous sodium hydrogen carbonate solution, and then a saturated aqueous sodium chloride solution in this order. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain 1.25 g of 4-methoxybenzyl [3-(cyanomethyl)phenyl]acetate as a yellow oily substance.

Workup

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with a 5% aqueous citric acid solution
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-e5e148dc3b444a1d8afd7f0dc883200f
Source dataset
uspto-grants-2013_07
Patent number
US08486970B2

Reaction notes

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