Pyridine → HCID 18332322, compound

HRID 2268727Notes

Reaction equation

HRID 2268727 reaction equation
[CH2:1]([N:3]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:4][CH2:5][CH2:6][OH:7])[CH3:2].N1C=CC=CC=1.[S:24](Cl)([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)(=[O:26])=[O:25].C(OCC)(=O)C>C(Cl)Cl.O>[CH2:1]([N:3]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:4][CH2:5][CH2:6][O:7][S:24]([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)(=[O:26])=[O:25])[CH3:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 15284069HCID 15284069, compound

Product 1

HCID 18332322HCID 18332322, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

N-Ethyl 3-benzyloxycarbonylamino-1-propanol (4.0 g) was dissolved in methylene chloride (20 ml), and to the resulting solution were added pyridine (1.8 ml) and tosyl chloride (3.9 g). The resultant mixture was stirred at room temperature for 2 days. Ethyl acetate and water were added to the reaction solution obtained. The organic layer so separated was washed with an aqueous potassium hydrogen sulfate solution and then with water and then dried over magnesium sulfate. The solvent was evaporated off from the solution, and the residue was purified by a silica gel chromatography, thus affording the titled compound (4.4 g; 69%).

Workup

  1. customobtained
  2. customThe organic layer so separated
  3. washwas washed with an aqueous potassium hydrogen sulfate solution
  4. dry with materialwith water and then dried over magnesium sulfate
  5. customThe solvent was evaporated off from the solution
  6. customthe residue was purified by a silica gel chromatography

Sources & evidence

ORD record
ord-399fc78e3a4a450bb6a7adc5a090e6b7
Source dataset
uspto-grants-2001_12
Patent number
US06329338B1

Reaction notes

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