Chloride → 1,3-Di(tert-butyloxycarbonylamino)-2-(p-toluenesulfonyloxy)propane

HRID 853201Notes

Reaction equation

HRID 853201 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([OH:20])[CH2:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[S:28](Cl)([C:31]1[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=1)(=[O:30])=[O:29].[Cl-]>ClCCl.O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([O:20][S:28]([C:31]1[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=1)(=[O:30])=[O:29])[CH2:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 312ChlorideHCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine2×HCID 375632tert-butyl N-{3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}carbamate

Product 1

HCID 140714761,3-Di(tert-butyloxycarbonylamino)-2-(p-toluenesulfonyloxy)propaneYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

1,3-di(tert-butyloxycarbonylamino)propan-2-ol (example 10a) (2.89 g, 10 mmol) and triethylamine (2.22 ml, 16 mmol) were dissolved in anhydrous dichloromethane (100 ml). The reaction mixture was cooled in an ice bath followed by dropwise addition of tosyl chloride (2.272 g, 12 mmol) dissolved in dichloromethane (30 ml). The reaction mixture was then stirred at room temperature for 72 hours. One equivalent of chloride and 1.6 of triethylamine were added after 48 hours. Water was added to stop the reaction and the medium was allowed to settle. The organic phase was washed several times with water. The aqueous phases were combined and extracted again with dichloromethane. The organic phase was dried on magnesium sulfate, filtered and the solvent was evaporated. The residue obtained (6.44 g) was purified by chromatography on silica gel (eluent:dichloromethane followed by dichloromethane/methanol 99:1) to yield the desired compound as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. customthe reaction
  3. washThe organic phase was washed several times with water
  4. extractionextracted again with dichloromethane
  5. customThe organic phase was dried on magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue obtained (6.44 g)
  9. customwas purified by chromatography on silica gel (eluent:dichloromethane followed by dichloromethane/methanol 99:1)

Sources & evidence

ORD record
ord-195eeae895c641f3a21167a7f945cfb1
Source dataset
uspto-grants-2007_08
Patent number
US07253296B2

Reaction notes

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