4-Toluenesulfonyl chloride → 3-[(tert-Butoxycarbonyl)amino]propyl 4-methylbenzene-1-sulfonate

HRID 1828953Notes

Reaction equation

HRID 1828953 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][OH:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[S:20](Cl)([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21]>C(Cl)Cl>[S:20]([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)([O:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamate

Product 1

HCID 131203023-[(tert-Butoxycarbonyl)amino]propyl 4-methylbenzene-1-sulfonateYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-t-Butoxycarbonylaminopropanol (10.0 g) is dissolved in methylene chloride (100 ml) and thereto are added triethylamine (8.66 g) and tosyl chloride (16.3 g) with stirring under ice cooling. The mixture is stirred at room temperature overnight. The reaction mixture is concentrated and the residue is dissolved in water-ethyl acetate, and the organic layer is separated, washed with an aqueous saturated saline solution, dried over sodium sulfate, and then distilled off the solvent. The residue is purified with a silica gel column chromatography to give 3-t-butoxycarbonylaminopropyl tosylate (15.37 g) as pale yellow oil.

Workup

  1. stirringThe mixture is stirred at room temperature overnight
  2. concentrationThe reaction mixture is concentrated
  3. dissolutionthe residue is dissolved in water-ethyl acetate
  4. customthe organic layer is separated
  5. washwashed with an aqueous saturated saline solution
  6. dry with materialdried over sodium sulfate
  7. distillationdistilled off the solvent
  8. customThe residue is purified with a silica gel column chromatography

Sources & evidence

ORD record
ord-58cae1b53b2f4588b4516f1de3c5e035
Source dataset
uspto-grants-2006_06
Patent number
US07060832B2

Reaction notes

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