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

HRID 444474ノート

反応式

HRID 444474 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 6375Nitromethane溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-659e7dac50c440afaa4c0773dcf98a99
出典データセット
uspto-grants-1981_04
特許番号
US04264597

反応ノート

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