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

HRID 356574Notes

Reaction equation

HRID 356574 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 with stirring triethylamine (8.66 g) and tosyl chloride (16.3 g) under ice-cooling, and the mixture is stirred at room temperature overnight. The reaction mixture is concentrated, and the residue is dissolved in a mixture of water and ethyl acetate. The organic layer is separated, washed with a saturated sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give 3-t-butoxycarbonylaminopropyl tosylate (15.37 g) as a pale yellow oil.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture is concentrated
  3. dissolutionthe residue is dissolved in a mixture of water and ethyl acetate
  4. customThe organic layer is separated
  5. washwashed with a saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a47e68aea12b452eba882e0f08e86a02
Source dataset
uspto-grants-1998_11
Patent number
US05837673

Reaction notes

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