Diisopropyl Ether → Benzhydryl 7-amino-3-allylthiomethyl-3-cephem-4-carboxylate

HRID 1463085ノート

反応式

HRID 1463085 の反応式
P(Cl)(Cl)(Cl)(Cl)Cl.C1(CC([NH:16][CH:17]2[C:45](=[O:46])[N:19]3[C:20]([C:29]([O:31][CH:32]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:30])=[C:21]([CH2:24][S:25][CH2:26][CH:27]=[CH2:28])[CH2:22][S:23][C@H:18]23)=O)C=CC=CC=1.C(=O)(O)[O-].[Na+].C(OC(C)C)(C)C>C(Cl)Cl.O.CO.N1C=CC=CC=1>[NH2:16][CH:17]1[C:45](=[O:46])[N:19]2[C:20]([C:29]([O:31][CH:32]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[O:30])=[C:21]([CH2:24][S:25][CH2:26][CH:27]=[CH2:28])[CH2:22][S:23][C@H:18]12

参加物

9

反応物 4

HCID 7914Diisopropyl EtherHCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 67712927Benzhydryl 7-(2-phenylacetamido)-3-allylthiomethyl-3-cephem-4-carboxylate

生成物 1

HCID 67712680Benzhydryl 7-amino-3-allylthiomethyl-3-cephem-4-carboxylate収率 37.3%

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒3 回

反応条件

温度
-20 °C

実験手順

To a suspension of phosphorus pentachloride (16.1 g) and pyridine (6.3 ml) in methylene chloride (100 ml) were added benzhydryl 7-(2-phenylacetamido)-3-allylthiomethyl-3-cephem-4-carboxylate (22 g) and methylene chloride (100 ml) at 5° C., and the mixture was stirred at the same temperature for an hour. After cooling to -20° C., methanol (10 ml) was added thereto, followed by stirring at -10° C. for half an hour. To this mixture was added water (10 ml) and stirred for 10 minutes. To the separated methylene chloride was added an aqueous solution of sodium bicarbonate until the pH value of the aqueous solution became 5.0, and the mixture was shaken. After separating out the organic layer, it was washed with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and evaporated to dryness. The residue obtained was pulverized with diisopropyl ether to give benzhydryl 7-amino-3-allylthiomethyl-3-cephem-4-carboxylate (6.5 g).

後処理

  1. stirringby stirring at -10° C. for half an hour
  2. stirringstirred for 10 minutes
  3. stirringthe mixture was shaken
  4. customAfter separating out the organic layer, it
  5. washwas washed with an aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated to dryness
  8. customThe residue obtained

出典と根拠

ORDレコード
ord-0c596a04e1454bac97fc13d79bbcd510
出典データセット
uspto-grants-1984_07
特許番号
US04462999

反応ノート

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