Chloroacetyl chloride → HCID 86630238, compound

HRID 424435Notes

Reaction equation

HRID 424435 reaction equation
Cl[CH2:2][C:3](Cl)=[O:4].[CH3:6][S:7]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C@H:17]([OH:27])[CH2:18][NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:13][CH:12]=1)(=[O:9])=[O:8].[OH-].[K+]>[OH-].[Na+].CC(O)C>[CH3:6][S:7]([O:10][C:11]1[CH:12]=[CH:13][C:14]([C@@H:17]2[O:27][CH2:2][C:3](=[O:4])[N:19]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:18]2)=[CH:15][CH:16]=1)(=[O:9])=[O:8]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 14797Potassium HydroxideHCID 86630236HCID 86630236, compound

Product 1

HCID 86630238HCID 86630238, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Chloroacetyl chloride (27.5 g, 243 mmol) was dropped to a solution of 4-((1S)-2-benzylamino-1-hydroxyethyl)phenyl methanesulfonate (71 g, 221 mmol) in 1N aqueous sodium hydroxide (330 ml) and stirred for one hour at room temperature. Resulting solution was extracted with chloroform, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. Potassium hydroxide (85%, 17.5 g, 265 mmol) was added to a solution of the resulting pale brown oil in 2-propanol (600 ml), and the mixture was stirred for 10 hours. The solvent was removed in vacuo and the residue was partitioned between water and chloroform. The organic layer was washed with 0.5 M hydrochloric acid, saturated sodium hydrogen carbonate, brine and dried over anhydrous magnesium sulfate. Removal of the solvent under reduced pressure furnished 4-((2S)-4-benzyl-5-oxo-morpholin-2-yl)phenyl methanesulfonate (79.8 g, 100%) as a brown oil.

Workup

  1. extractionResulting solution was extracted with chloroform
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was removed under reduced pressure
  4. stirringthe mixture was stirred for 10 hours
  5. customThe solvent was removed in vacuo
  6. customthe residue was partitioned between water and chloroform
  7. washThe organic layer was washed with 0.5 M hydrochloric acid, saturated sodium hydrogen carbonate, brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-4991c66c0a0f45a5bea2e7619dd7ad87
Source dataset
uspto-grants-2012_01
Patent number
US08106045B2

Reaction notes

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