Phosphorus oxychloride → Benzyl 5-methyl-2-(1-methylcyclohexyl)-4-oxazoleacetate

HRID 746030Notes

Reaction equation

HRID 746030 reaction equation
[CH3:1][C:2]1([C:8]([NH:10][CH:11]([C:23](=[O:25])[CH3:24])[CH2:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH3:24][C:23]1[O:25][C:8]([C:2]2([CH3:1])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)=[N:10][C:11]=1[CH2:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 23311271Benzyl 3-(1-methylcyclohexylcarbonylamino)-4-oxovalerate

Product 1

HCID 53939088Benzyl 5-methyl-2-(1-methylcyclohexyl)-4-oxazoleacetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of benzyl 3-(1-methylcyclohexylcarbonylamino)-4-oxovalerate (1.2 g), toluene (20 ml) and phosphorus oxychloride (2.0 ml) was refluxed with stirring for 4 hours. The solvent was distilled off and aqueous sodium hydrogen carbonate was added. The mixture was extracted with ethyl ether and the ethyl ether layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off and the residue was purified by chromatography on silica gel (13 g) [eluent: hexaneacetone (9:1)] to give benzyl 5-methyl-2-(1-methylcyclohexyl)- 4-oxazoleacetate; yield 1.0 g (87.7%).

Workup

  1. temperaturewas refluxed
  2. distillationThe solvent was distilled off
  3. additionaqueous sodium hydrogen carbonate was added
  4. extractionThe mixture was extracted with ethyl ether
  5. washthe ethyl ether layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was then distilled off
  8. customthe residue was purified by chromatography on silica gel (13 g) [eluent: hexaneacetone (9:1)]

Sources & evidence

ORD record
ord-4736b1a4c066457ba543287808a066df
Source dataset
uspto-grants-1986_07
Patent number
US04602027

Reaction notes

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