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

HRID 234178노트

반응식

HRID 234178 반응식
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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 1049Pyridine용매HCID 6344Dichloromethane용매3회

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온도
-20 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-97a27edff9454cfba8228cba52a87c02
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05594132

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