Hydrochloric Acid → tert-Butyl 3-sulfanylazetidine-1-carboxylate

HRID 241636Notes

Reaction equation

HRID 241636 reaction equation
C([S:4][CH:5]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+].Cl>CO>[SH:4][CH:5]1[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 18363257Tert-butyl 3-(acetylthio)azetidine-1-carboxylate

Product 1

HCID 58513580tert-Butyl 3-sulfanylazetidine-1-carboxylateYield 101.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Mixture of tert-butyl 3-(acetylthio)azetidine-1-carboxylate (STEP C, 700 mg, 3.03 mmol), methanol (10 mL) and potassium carbonate (836 mg, 6.05 mol) was stirred at 50° C. for 2 h and cooled to room temperature. To the reaction mixture was added 2 mol/L hydrochloric acid for solution acidified (pH <4). The resulting solution was extracted with diethyl ether (30 mL×2). The organic layer was combined and washed with water (30 mL×2) and brine (30 mL). The extract was dried with magnesium sulfate and concentrated. Resulting crude product (581 mg) was used without further purification.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe resulting solution was extracted with diethyl ether (30 mL×2)
  3. washwashed with water (30 mL×2) and brine (30 mL)
  4. dry with materialThe extract was dried with magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1976d53515af40f5b89eae1279a0532d
Source dataset
uspto-grants-2014_02
Patent number
US08653063B2

Reaction notes

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