Acetyl chloride → HCID 178457297, compound

HRID 654986Notes

Reaction equation

HRID 654986 reaction equation
O=[C:2]([CH:8]([CH3:18])[CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][C:4]([O:6][CH3:7])=[O:5].[CH2:19]([NH2:22])[CH:20]=[CH2:21].[C:23](Cl)(=[O:25])[CH3:24]>CO>[C:23]([C:3](=[C:2]([NH:22][CH2:19][CH:20]=[CH2:21])[CH:8]([CH3:18])[CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4]([O:6][CH3:7])=[O:5])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 7853AllylamineHCID 14348494HCID 14348494, compound

Product 1

HCID 178457297HCID 178457297, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
40 °C

Procedure

Methyl 3-oxo-4-methyl-5-benzyloxypentanoate (1.11 g; 4.43 mmole) was dissolved in dry methanol (5 ml), allylamine (1.26 g) and molecular sieve 3A (0.6 g) were added thereto and then a solution of acetyl chloride (1.04 g; 13.3 mmole) in dry methanol (2 ml) was added thereto with icecooling, followed by stirring at 40° C. for 12 hours. The molecular sieve was removed by filtration, and the filtrate was diluted with ethyl acetate. The reaction mixture was washed successively with a saturated sodium bicarbonate solution and an aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was dissolved in toluene (5 ml), and gaseous ketene was introduced therein at room temperature. After completion of the reaction, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to give methyl 2-acetyl-3-allylamino-4-methyl-5-benzyloxy-2-pentenoate.

Workup

  1. customThe molecular sieve was removed by filtration
  2. additionthe filtrate was diluted with ethyl acetate
  3. washThe reaction mixture was washed successively with a saturated sodium bicarbonate solution
  4. dry with materialan aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in toluene (5 ml)
  7. additiongaseous ketene was introduced
  8. customat room temperature
  9. customAfter completion of the reaction
  10. customthe solvent was removed under reduced pressure
  11. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0694dfa53ca34ae5b41ef2823b47ba3f
Source dataset
uspto-grants-1992_07
Patent number
US05134231

Reaction notes

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