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

HRID 1388175Notes

Reaction equation

HRID 1388175 reaction equation
N1C=CC=CC=1.[C:7]([O:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][OH:18])=[O:13])([CH3:10])([CH3:9])[CH3:8].[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>O>[S:25]([O:18][CH2:17][CH2:16][CH2:15][NH:14][C:12]([O:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:13])([C:22]1[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=1)(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 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 962WaterSolvent

Procedure

Into 50 ml of pyridine, was dissolved 2.95 g (16.9 mmoles) of 3-tert-butoxycarbonylamino-1-propanol. To this solution, while being cooled in ice under an argon atmosphere, was added dropwise over a period of 40 minutes a pyridine solution containing 3.36 g (17.7 mmoles) of p-toluenesulfonyl chloride. The mixture was left standing overnight at 7° C., admixed with a small quantity 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 a developing solvent. The Fraction Nos. 35 to 68 (each 15 ml in volume) were combined and evaporated to dryness to obtain 3.06 g (55% yield) of O-tosyl-3-tert-butoxycarbonylamino-1-propanol in the form of colorless oil.

Workup

  1. temperatureTo this 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-31c1c33f2254442b9e8fce7d5301a56e
Source dataset
uspto-grants-1984_02
Patent number
US04430346

Reaction notes

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