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

HRID 1706520노트

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HRID 1706520 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23994Zinc촉매2회HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-51b5cfdef00844dd84efbb9839984b3c
출처 데이터셋
uspto-grants-1980_06
특허 번호
US04207234

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