Phenylacetyl chloride → HCID 13632914, compound

HRID 1252498Notes

Reaction equation

HRID 1252498 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@@H:5]1[CH2:9][CH2:8][CH2:7][NH:6]1.C(N(CC)CC)C.[C:18]1([CH2:24][C:25](Cl)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:10])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:25](=[O:26])[CH2:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471Triethylamine2×HCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 13632914HCID 13632914, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Proline methyl ester hydrochloride (3.3 g) and triethylamine (2.8 ml) were suspended in dry methylene chloride (30 ml). Under cooling, phenylacetylchloride (3.4 g) and triethylamine (3.1 ml) were simultaneously added dripwise to the suspension. Thereafter, the mixture was stirred at room temperature for 2 hours, and the reaction mixture was washed successively with water, 1N HCl, water, saturated aqueous sodium bicarbonate and brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off under vacuum. The resulting crude product was purified by medium-pressure liquid column chromatography on silica gel (solvent: carbon tetrachloride) to obtain the end compound an an oil (3.7 g).

Workup

  1. temperatureUnder cooling
  2. washthe reaction mixture was washed successively with water, 1N HCl, water, saturated aqueous sodium bicarbonate and brine
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under vacuum
  5. customThe resulting crude product was purified by medium-pressure liquid column chromatography on silica gel (solvent: carbon tetrachloride)

Sources & evidence

ORD record
ord-32b4384140ce4b2fae972d8a4c8ec761
Source dataset
uspto-grants-1988_05
Patent number
US04743616

Reaction notes

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