Ethanol → HCID 70390712, compound

HRID 653291Notes

Reaction equation

HRID 653291 reaction equation
[N:1]([CH2:4][C@H:5]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH3:19])[C:7](=[O:20])[C@H:6]1[NH:21][C:22](=[O:30])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[N+]=[N-].[CH2:31]([OH:33])[CH3:32]>[Pd]>[C:31]([NH:1][CH2:4][C@H:5]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH3:19])[C:7](=[O:20])[C@H:6]1[NH:21][C:22](=[O:30])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:33])[CH3:32]

Participants

4

Reactant 2

HCID 702EthanolHCID 86740464cis-4-Azidomethyl-1-(2,4-dimethoxybenzyl)-3-phenylacetamido-2-oxoazetidine

Product 1

HCID 70390712HCID 70390712, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
0 °C

Procedure

To a solution of 449 mg of cis-4-azidomethyl-1-(2,4-dimethoxybenzyl)-3-phenylacetamido-2-oxoazetidine in 80 ml of ethanol is added 200 mg of 10% palladium on charcoal, and the mixture is subjected to hydrogenation for 1.5 hours at room temperature and atmospheric pressure. The reaction mixture is filtered to remove the catalyst and the filtrate is concentrated to dryness in vacuo. The residue is taken up in 30 ml of methylene chloride. Under stirring at 0° C., 0.20 ml of triethylamine is added to the resulting methylene chloride solution, and a solution of 0.10 ml of acetyl chloride in methylene chloride is added dropwise over 10 minutes thereto. The reaction mixture is stirred for 40 minutes and then washed with dilute hydrochloric acid, water, an aqueous sodium hydrogen carbonate solution and an aqueous sodium chloride solution in this order, and dried over magnesium sulfate, and the solvent is distilled off in vacuo. Ethyl acetate is added to the residue and the resulting crystals are collected by filtration to give cis- 4-acetamidomethyl-1-(2,4-dimethoxybenzyl)-3-phenylacetamido-2-oxoazetidine, m.p. 205°-207° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate is concentrated to dryness in vacuo
  4. addition0.20 ml of triethylamine is added to the resulting methylene chloride solution
  5. additiona solution of 0.10 ml of acetyl chloride in methylene chloride is added dropwise over 10 minutes
  6. stirringThe reaction mixture is stirred for 40 minutes
  7. washwashed with dilute hydrochloric acid, water
  8. dry with materialan aqueous sodium hydrogen carbonate solution and an aqueous sodium chloride solution in this order, and dried over magnesium sulfate
  9. distillationthe solvent is distilled off in vacuo
  10. additionEthyl acetate is added to the residue
  11. filtrationthe resulting crystals are collected by filtration

Sources & evidence

ORD record
ord-c7ac9c4dc97a4097b91ecf15efc5ec14
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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