Sodium Bicarbonate → 3-[(Phenylacetyl)amino]-2-azetidinone

HRID 1706520ノート

反応式

HRID 1706520 の反応式
ClC(Cl)(Cl)COC(NC([N:12]1[CH2:15][CH:14]([NH:16][C:17](=[O:25])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]1=[O:26])C(C)C)=O.C(=O)(O)[O-].[Na+]>C(O)(=O)C.[Zn]>[C:19]1([CH2:18][C:17]([NH:16][CH:14]2[CH2:15][NH:12][C:13]2=[O:26])=[O:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

5

反応物 2

HCID 516892Sodium BicarbonateHCID 536478601-[1-(2,2,2-Trichloroethoxycarbonylamino)-2-methylpropyl]-3-(2-phenylacetamido)-2-azetidinone

生成物 1

HCID 132120483-[(Phenylacetyl)amino]-2-azetidinone収率 58.6%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒2 回HCID 176Acetic Acid溶媒

実験手順

1-[1-(2,2,2-Trichloroethoxycarbonylamino)-2-methylpropyl]-3-(2-phenylacetamido)-2-azetidinone (1.13 g.) was dissolved in a 90% acetic acid aqueous solution (20 ml.), and the solution was cooled to 5° C. (Zinc powder (1.62 g.) was added dropwise to said solution in 5 minutes, and the mixture was stirred for 30 minutes. Furthermore, zinc powder (1.62 g.) was added to said mixture, and the mixture was stirred for 2 days. The reaction mixture was neutralized with a sodium bicarbonate aqueous solution, and extracted with methylene chloride. The extract was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off from the solution. The residue (0.65 g.) was subjected to preparative thin layer chromatography using silica.gel [developing solvent; a mixed solvent of ethyl acetate, ethyl methyl ketone, water and formic acid (volume ratio 5:3:1:1)], isolated and purified to give 3-(2-phenylacetamido)-2-azetidinone (0.3 g.). Mp 190° to 192° C.

後処理

  1. additionwas added dropwise
  2. customin 5 minutes
  3. stirringthe mixture was stirred for 2 days
  4. extractionextracted with methylene chloride
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off from the solution
  8. customa mixed solvent of ethyl acetate, ethyl methyl ketone, water and formic acid (volume ratio 5:3:1:1)], isolated
  9. custompurified

出典と根拠

ORDレコード
ord-51b5cfdef00844dd84efbb9839984b3c
出典データセット
uspto-grants-1980_06
特許番号
US04207234

反応ノート

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