Phenylacetyl chloride → HCID 70390633, compound

HRID 653285Notes

Reaction equation

HRID 653285 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]([C@H:12]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=2[O:25][CH3:26])[C:14](=[O:27])[C@H:13]1[NH2:28])=[O:11].[C:29]1([CH2:35][C:36](Cl)=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[CH3:8][O:9][C:10]([C@H:12]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=2[O:25][CH3:26])[C:14](=[O:27])[C@H:13]1[NH:28][C:36](=[O:37])[CH2:35][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:11]

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 14095500HCID 14095500, compound

Product 1

HCID 70390633HCID 70390633, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under ice-cooling and stirring, 2.10 ml of triethylamine is added to a solution of 2.94 g of cis-3-amino-1-(2,4-dimethoxybenzyl)-2-oxoazetidine-4-carboxylic acid methyl ester in 40 ml of methylene chloride, and a solution of 2.31 g of phenylacetyl chloride in 15 ml of methylene chloride is then added dropwise over 1 hour. The stirring is continued for another one hour under ice-cooling, and the reaction mixture is then washed successively with dilute hydrochloric acid, 5% aqueous sodium hydrogen carbonate and an aqueous sodium chloride solution, and dried over magnesium sulfate, and the solvent is distilled off in vacuo. Ether is added to the residue and the precipitated crystals are collected by filtration to give cis-1-(2,4-dimethoxybenzyl)-3-phenylacetamido-2-oxoazetidine-4-carboxylic acid methyl ester, m.p. 124°-126° C.

Workup

  1. temperatureUnder ice-cooling
  2. temperaturecooling
  3. washthe reaction mixture is then washed successively with dilute hydrochloric acid, 5% aqueous sodium hydrogen carbonate
  4. dry with materialan aqueous sodium chloride solution, and dried over magnesium sulfate
  5. distillationthe solvent is distilled off in vacuo
  6. additionEther is added to the residue
  7. filtrationthe precipitated crystals are collected by filtration

Sources & evidence

ORD record
ord-09874eb17f0e44a8bbcaac08df4feb1d
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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