Pyridine → 7-Phenoxyacetamido-3-methyl-3-cephem-4-carboxylic acid

HRID 647778

反応式

HRID 647778 の反応式
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:24](=[O:25])[N:14]2[CH:15]([C:21]([OH:23])=[O:22])[C:16]([CH3:20])([CH2:18]Br)[S:17][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.C(OCC)(=O)C>C1C=CC=CC=1>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:24](=[O:25])[N:14]2[C:15]([C:21]([OH:23])=[O:22])=[C:16]([CH3:20])[CH2:18][S:17][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 1049Pyridine2 回HCID 8857Ethyl AcetateHCID 128952582-Bromomethyl-2-methyl-6-(2-phenoxyacetamido)penam-3-carboxylic acid

生成物 1

HCID 155734007-Phenoxyacetamido-3-methyl-3-cephem-4-carboxylic acid収率 71.8%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

6-(2-phenoxyacetamido)-2-methyl-2-bromomethylpenam-3-carboxylic acid (429 mg.) was suspended in dry benzene (10 cc), and pyridine (400 mg.) and trimethylsilychloride (5 cc) were added thereto. The mixture was stirred for 1.5 hours at room temperature and pyridine (400 mg.) was added thereto. The mixture was heated under reflux for 3 hours, mixed with ethyl acetate (30 cc). washed with dilute phosphoric acid and further with an aqueous solution saturated with sodium chloride, dried and then concentrated. A small amount of ethyl acetate was added to the residue and the precipitate was collected by filtration to yield crystals (250 mg.) of 7-(2-phenoxyacetamido)-3-methyl-3-cephem-4-carboxylic acid, m.p. 170.5°-172° C.

後処理

  1. additionwere added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 3 hours
  4. washwashed with dilute phosphoric acid and further with an aqueous solution saturated with sodium chloride
  5. customdried
  6. concentrationconcentrated
  7. additionA small amount of ethyl acetate was added to the residue
  8. filtrationthe precipitate was collected by filtration

出典と根拠

ORDレコード
ord-4f0588dd3a694b089654c00ccefc391f
出典データセット
uspto-grants-1983_10
特許番号
US04410458

関連ノート

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