Methanesulfonic Acid → HCID 57634629, compound

HRID 2109827Notes

Reaction equation

HRID 2109827 reaction equation
CS(O)(=O)=O.[C:6]([NH:9][CH2:10][C:11]([N:13]([CH2:22][CH:23](OC)OC)[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)=[O:12])(=[O:8])[CH3:7].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[C:6]([N:9]1[CH:23]=[CH:22][N:13]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[C:11](=[O:12])[CH2:10]1)(=[O:8])[CH3:7]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 10340Sodium CarbonateHCID 57634628HCID 57634628, compound

Product 1

HCID 57634629HCID 57634629, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methanesulfonic acid (314 g) in dichloromethane (10 L) at room temperature, a solution of N2-acetyl-N1-(2,2-dimethoxyethyl)-N1-(4-fluoro-benzyl)glycinamide (438 g, 1.07 mol) in dichloromethane (2 L) was added slowly over a period of 2 h. The reaction mixture was stirred at room temperature overnight and treated with saturated aqueous sodium carbonate (3 L). The organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. To the residual oil, ethyl acetate (1 L) was added and stirred at room temperature. The solid precipitated was filtered to provide the title compound.

Workup

  1. extractionThe organic extract
  2. washwas washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. additionTo the residual oil, ethyl acetate (1 L) was added
  7. stirringstirred at room temperature
  8. customThe solid precipitated
  9. filtrationwas filtered

Sources & evidence

ORD record
ord-38252e0f46c845e3856eb90f3dcc4478
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

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