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

HRID 463450Notes

Reaction equation

HRID 463450 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:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.O>N1C=CC=CC=1>[S:19]([O:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])([C:16]1[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamate

Product 1

HCID 131203023-[(tert-Butoxycarbonyl)amino]propyl 4-methylbenzene-1-sulfonateYield 55%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Into 50 mL of pyridine was dissolved 2.95 g (16.9 mmoles) of 3-tert-butoxycarbonylamino-1-propanol. To the solution, while being cooled in ice under an argon atmosphere, was added dropwise over a period of 40 minutes a solution of 3.36 g (17.7 mmoles) of p-toluenesulfonyl chloride in pyridine. The mixture was left standing overnight at 7° C., then admixed with a small volume of water, and evaporated to dryness. The residue was dissolved in 200 mL of chloroform, washed successively with 5% aqueous potassium hydrogensulfate solution, saturated aqueous sodium hydrogencarbonate solution, and water, then dried over anhydrous sodium sulfate, evaporated to dryness, and subjected to column chromatography using 120 g of silica gel (Wako-Gel®C-200) and a toluene-ethyl acetate (8:1 by volume) mixture as developing solvent. Fraction Nos. 35 to 68 (each 15 mL in volume) were combined and evaporated to dryness to yield 3.06 g (55% yield) of O-tosyl-3-tert-butoxycarbonylamino-1-propanol in colorless oily form.

Workup

  1. temperatureTo the solution, while being cooled in ice under an argon atmosphere
  2. waitThe mixture was left
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in 200 mL of chloroform
  5. washwashed successively with 5% aqueous potassium hydrogensulfate solution, saturated aqueous sodium hydrogencarbonate solution, and water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated to dryness
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-51d359f7c3504b0ea6e17924bb7c9e7a
Source dataset
uspto-grants-1985_05
Patent number
US04518802

Reaction notes

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