Hydrochloric Acid → 7beta-(2-Phenoxyacetamido)-2-oxo-3-cephem-4-carboxylic acid

HRID 444474노트

반응식

HRID 444474 반응식
[O:1]([CH2:8][C:9]([NH:11][C@@H:12]1[C:30](=[O:31])[N:14]2[C:15]([C:20]([O:22]CC3C=CC=CC=3)=[O:21])=[CH:16][C:17](=[O:19])[S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(OC)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl.[N+](C)([O-])=O>[O:1]([CH2:8][C:9]([NH:11][C@@H:12]1[C:30](=[O:31])[N:14]2[C:15]([C:20]([OH:22])=[O:21])=[CH:16][C:17](=[O:19])[S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 13117288Benzyl 7beta-(2-phenoxyacetamido)-2-oxo-3-cephem-4-carboxylate

생성물 1

HCID 131172907beta-(2-Phenoxyacetamido)-2-oxo-3-cephem-4-carboxylic acid수율 80.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 6375Nitromethane용매

실험 절차

To a solution of benzyl 7β-(2-phenoxyacetamido)-2-oxo-3-cephem-4-carboxylate (369 mg) in methylene chloride (15 ml) were added successively anisole (1.37 ml) and a solution of aluminum chloride (560 mg) in nitromethane (5 ml) under ice-cooling. The mixture was stirred for 25 minutes at the same temperature and poured into a mixture of methylene chloride and dil. hydrochloric acid. The organic layer was separated, washed with an aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated to dryness. After addition of diisopropyl ether to the residue, the precipitates were collected by filtration and then washed with a small amount of diethyl ether to give 7β-(2-phenoxyacetamido)-2-oxo-3-cephem-4-carboxylic acid (235 mg). mp 158° to 160° C. (dec.).

후처리

  1. customThe organic layer was separated
  2. washwashed with an aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to dryness
  5. additionAfter addition of diisopropyl ether to the residue
  6. filtrationthe precipitates were collected by filtration
  7. washwashed with a small amount of diethyl ether

출처 및 근거

ORD 기록
ord-659e7dac50c440afaa4c0773dcf98a99
출처 데이터셋
uspto-grants-1981_04
특허 번호
US04264597

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