Hexamethylphosphoramide → Desethyl-etomidate

HRID 259430Notes

Reaction equation

HRID 259430 reaction equation
[Na+].[C:2]1([CH:8]([N:10]2[C:14]([C:15]([O-:17])=[O:16])=[CH:13][N:12]=[CH:11]2)[CH3:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CN(C)P(=O)(N(C)C)N(C)C>O>[C:2]1([CH:8]([N:10]2[C:14]([C:15]([OH:17])=[O:16])=[CH:13][N:12]=[CH:11]2)[CH3:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 12679HexamethylphosphoramideHCID 24758Sodium hydrideHCID 23693872HCID 23693872, compound

Product 1

HCID 297427Desethyl-etomidate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 14.3 parts of (-)-1-(1-phenylethyl)-1H-imidazole-5-carboxylic acid sodium salt, 1.9 parts of a 61.8% suspension of sodium hydride in mineral oil and 60 parts of hexamethylphosphoric triamide is stirred for 20 hours at 100° C. under Argon atmosphere. The mixture is allowed to cool to room temperature and poured onto 150 parts of water. The whole is washed three times with 200 parts of dichloromethane. The aqueous phase is neutralized (pH 7) with acetic acid and the product is allowed to crystallize. The product is filtered off, dried and recrystallized from ethanol, yielding (±)-1-(1-phenylethyl)-1H-imidazole-5-carboxylic acid; m.p. 188° C.

Workup

  1. temperatureto cool to room temperature
  2. washThe whole is washed three times with 200 parts of dichloromethane
  3. customto crystallize
  4. filtrationThe product is filtered off
  5. customdried
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a66ebd993bca4849b5efc0f60599907f
Source dataset
uspto-grants-1977_07
Patent number
US04038286

Reaction notes

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