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

HRID 1200115Notes

Reaction equation

HRID 1200115 reaction equation
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

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-20 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6373f738d8084346906b74fd765f6ff0
Source dataset
uspto-grants-1990_02
Patent number
US04904652

Reaction notes

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