Hydrochloric Acid → (S)-2-((tert-butoxycarbonyl)amino)propyl 4-methylbenzenesulfonate

HRID 2368057Notes

Reaction equation

HRID 2368057 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].[S:13](Cl)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14].Cl>N1C=CC=CC=1>[CH3:20][C:19]1[CH:21]=[CH:22][C:16]([S:13]([O:1][CH2:2][C@@H:3]([NH:5][C:6]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:12])[CH3:4])(=[O:15])=[O:14])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chloride2×HCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate

Product 1

HCID 13200311(S)-2-((tert-butoxycarbonyl)amino)propyl 4-methylbenzenesulfonateYield 71.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of tert-butyl [(1S)-2-hydroxy-1-methylethyl]carbamate (10.0 g), tosyl chloride (12.0 g) and pyridine (100 mL) was stirred for 30 min under ice-cooling, and at room temperature for 2 hr. Tosyl chloride (6.0 g) was further added to the reaction mixture, and the mixture was stirred at room temperature overnight. 0.5M Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a white solid (13.5 g).

Workup

  1. temperaturecooling
  2. waitat room temperature for 2 hr
  3. stirringthe mixture was stirred at room temperature overnight
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe obtained organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8561fd29bbbf4be19aa28316fa6d609a
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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