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

HRID 462906Notes

Reaction equation

HRID 462906 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

To a solution of 2.95 g (16.9 mmoles) of 3-tert-butoxycarbonylamino-1-propanol in 50 ml of pyridine, 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., 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 and evaporated to dryness. The residue was subjected to column chromatography using 120 g of silica gel (Wakogel® C-200) and a toluene-ethyl acetate (8:1 by volume) mixture as developing solvent (15 ml fraction size). Fractions No. 35 to No. 68 were combined and evaporated to dryness to yield 3.06 g (55% yield) of O-tosyl-3-tert-butoxycarbonylamino-1-propanol, a colorless oily substance.

Workup

  1. waitThe mixture was left
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in 200 ml of chloroform
  4. washwashed successively with 5% aqueous potassium hydrogensulfate solution, saturated aqueous sodium hydrogencarbonate solution and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-800c5e1f92094077867083d355d866c1
Source dataset
uspto-grants-1985_05
Patent number
US04518532

Reaction notes

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