Sodium Hydroxide → HCID 23077370, compound

HRID 1373503Notes

Reaction equation

HRID 1373503 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH3:19])[CH2:13][S:14]([O:16]CC)=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH3:19])[CH2:13][S:14]([OH:16])=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23077363HCID 23077363, compound

Product 1

HCID 23077370HCID 23077370, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (7 ml) was dissolved 2.2 g (7.4 mmol) of ethyl 2-(benzyloxycarbonylamino)propane-1-sulfinate, and 3.2 g (8 mmol) of 10% aqueous sodium hydroxide solution was slowly dropped thereinto under ice-cooling. The reaction was carried out at room temperature for 1 hour, after which the ethanol was distilled off and water was added to the residue, followed by two runs of extraction with methyl t-butyl ether. The aqueous layer was acidified with concentrated hydrochloric acid, followed by three runs of extraction with ethyl acetate. The extract solution was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off and the crude crystals thus obtained were washed twice with a solvent (hexane:ethyl acetate=4:1) to obtain 1.73 g (yield 91%) of 2-(benzyloxycarbonylamino)propane-1-sulfinic acid.

Workup

  1. additionwas slowly dropped
  2. temperatureunder ice-cooling
  3. distillationafter which the ethanol was distilled off
  4. additionwater was added to the residue
  5. extractionfollowed by two runs of extraction with methyl t-butyl ether
  6. extractionfollowed by three runs of extraction with ethyl acetate
  7. washThe extract solution was washed with saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off
  10. customthe crude crystals thus obtained
  11. washwere washed twice with a solvent (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-34e034dd115a4597ac737d53b49c5b9c
Source dataset
uspto-grants-2007_01
Patent number
US07161032B2

Reaction notes

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