Ethanol → HCID 70390712、化合物

HRID 978878ノート

反応式

HRID 978878 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 70390712HCID 70390712、化合物

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f91639b2ac904538962599d52ce39e1d
出典データセット
uspto-grants-1987_05
特許番号
US04665067

反応ノート

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