Phosphorus pentachloride → 3-(2-Hydroxyimino-2-phenylacetamido)-1-(2-methoxycarbonyl-1-phenylethyl)-2-azetidinone

HRID 1706523노트

반응식

HRID 1706523 반응식
[NH2:1][CH:2]1[CH2:5][N:4]([CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][C:8]([O:10][CH3:11])=[O:9])[C:3]1=[O:18].C[Si](C([Si](C)(C)C)C(N)=O)(C)C.ClC(Cl)C([O:35][N:36]=[C:37]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:38](O)=[O:39])=O.P(Cl)(Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[OH:35][N:36]=[C:37]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:38]([NH:1][CH:2]1[CH2:5][N:4]([CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][C:8]([O:10][CH3:11])=[O:9])[C:3]1=[O:18])=[O:39]

참가 물질

7

반응물 5

HCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 11708267BistrimethylsilylacetamidHCID 53748477HCID 53748477, 화합물HCID 539654873-Amino-1-(2-methoxycarbonyl-1-phenylethyl)-2-azetidinone

생성물 1

HCID 867370493-(2-Hydroxyimino-2-phenylacetamido)-1-(2-methoxycarbonyl-1-phenylethyl)-2-azetidinone수율 35.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

3-Amino-1-(2-methoxycarbonyl-1-phenylethyl)-2-azetidinone (1.3 g.) was added to methylene chloride (30 ml.), and then bis(trimethylsilyl)acetamide (3.05 g.) was added thereto. To the solution, there was dropwise added methylene chloride (30 ml.) solution containing 2-(2,2-dichloroacetoxyimino)-2-phenylacetic acid (1.9 g.) and phosphorus pentachloride (1.7 g.) at -40° to -35° C. in the course of 5 minutes. The mixture was stirred at the same temperature for 15 minutes and additionally stirred at 5° C. for 15 minutes. An aqueous sodium bicarbonate was added to the reaction mixture and the mixture was stirred at ambient temperature for 5 minutes. The methylene chloride layer was separated from the mixture, washed with dilute hydrochloric acid, an aqueous sodium bicarbonate and water in turn, and then dried over magnesium sulfate. The solvent was removed by distillation under reduced pressure to give a residue, which was subjected to column chromatography on silica gel (100 g.). Elution was carried out with chloroform and the fractions containing a desired compound were collected. The solvent was distilled off from the eluate under reduced pressure to give crystals of 3-(2-hydroxyimino-2-phenylacetamido)-1-(2-methoxycarbonyl-1-phenylethyl)-2-azetidinone (0.74 g.).

후처리

  1. stirringadditionally stirred at 5° C. for 15 minutes
  2. stirringthe mixture was stirred at ambient temperature for 5 minutes
  3. customThe methylene chloride layer was separated from the mixture
  4. washwashed with dilute hydrochloric acid
  5. dry with materialan aqueous sodium bicarbonate and water in turn, and then dried over magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customto give a residue, which
  8. washElution
  9. additionthe fractions containing a desired compound
  10. customwere collected
  11. distillationThe solvent was distilled off from the eluate under reduced pressure

출처 및 근거

ORD 기록
ord-6de8606e1af6460abbe3e715c9393a68
출처 데이터셋
uspto-grants-1980_06
특허 번호
US04207234

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