Pyridine → HCID 19024523, compound

HRID 1033861Notes

Reaction equation

HRID 1033861 reaction equation
[C:1]([C:4]1[N:5]=[CH:6][O:7][C:8]=1[CH2:9][CH2:10][NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])([OH:3])=[O:2].N1C=CC=CC=1.[C:28](O)([CH3:31])([CH3:30])[CH3:29].P(Cl)(Cl)(Cl)=O>C(Cl)(Cl)Cl>[C:28]([O:2][C:1]([C:4]1[N:5]=[CH:6][O:7][C:8]=1[CH2:9][CH2:10][NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:3])([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6386tert-ButanolHCID 24813Phosphorus oxychlorideHCID 19024530HCID 19024530, compound

Product 1

HCID 19024523HCID 19024523, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 2.9 g of 4-carboxy-5-{2-(benzyloxycarbonylamino)ethyl}oxazole, 4.9 g of pyridine, 6 ml of tert-butyl alcohol and 50 ml of chloroform was added dropwise 1.84 g of phosphoryl chloride at -10° C., and the mixture was stirred at the same temperature for 1 hour and further at room temperature overnight. The mixture was washed and dried, and then the solvent was removed. The residue was purified by silica gel chromatography to obtain 2.85 g of 4-tert-butoxycarbonyl-5-{2-(benzyloxycarbonylamino)ethyl}oxazole as a colorless oily product.

Workup

  1. washThe mixture was washed
  2. customdried
  3. customthe solvent was removed
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9e74fa030ad146d7b986d3f170fd26ac
Source dataset
uspto-grants-1994_05
Patent number
US05312826

Reaction notes

Loading…