Phosphoric Acid → HCID 70504140, compound

HRID 1463146Notes

Reaction equation

HRID 1463146 reaction equation
S1C=CC=C1CC([NH:9][CH:10]1[C:39](=[O:40])[N:12]2[C:13]([C:23]([O:25][CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])=[C:14]([CH2:18][O:19][C:20](=[O:22])[CH3:21])[C@H:15]([CH3:17])[S:16][C@H:11]12)=O.P(Cl)(Cl)(Cl)(Cl)Cl.OP([O-])([O-])=O.[K+].[K+].OP(O)(O)=O>C(Cl)Cl.CO.N1C=CC=CC=1>[NH2:9][CH:10]1[C:39](=[O:40])[N:12]2[C:13]([C:23]([O:25][CH:26]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[O:24])=[C:14]([CH2:18][O:19][C:20](=[O:22])[CH3:21])[C@H:15]([CH3:17])[S:16][C@H:11]12

Participants

8

Reactant 4

HCID 1004Phosphoric AcidHCID 24450Potassium Phosphate, DibasicHCID 24819Phosphorus pentachlorideHCID 70505024HCID 70505024, compound

Product 1

HCID 70504140HCID 70504140, compoundYield 117.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A 6.8 ml portion of pyridine was added to a solution of 4 g of diphenylmethyl 7-(2-thienylacetamido)-2β-methyl-3-acetoxymethylceph-3-em-4-carboxylate in 170 ml of CH2Cl2, and 4.35 g of PCl5 was then added to the mixture at -12° C., followed by stirring at the same temperature for 45 minutes. 45 ml of MeOH was added in once to the mixture, followed by stirring at -10° C. for 30 minutes and further at room temperature for 1 hour. 100 ml of 0.5M K2HPO4 solution and further 25% H3PO4 were added to the reaction solution to adjust to pH 1.5, followed by stirring for 45 minutes and separating out the CH2Cl2 layer. The layer was washed with saturated aqueous NaCl solution and dried over MgSO4, and the CH2Cl2 was distilled off under reduced pressure. The residue was added on a column of silica gel, and the fractions eluted with CH2Cl2.AcOEt (10:1) were collected to distill off the solvent under reduced pressure. Petroleum ether was added to the residue, thus yielding 3.7 g (87%) of crystals of diphenylmethyl 7-amino-2β-methyl-3-acetoxymethylceph-3-em-4-carboxylate,

Workup

  1. additionwas then added to the mixture at -12° C.
  2. stirringby stirring at -10° C. for 30 minutes and further at room temperature for 1 hour
  3. stirringby stirring for 45 minutes
  4. customseparating out the CH2Cl2 layer
  5. washThe layer was washed with saturated aqueous NaCl solution
  6. dry with materialdried over MgSO4
  7. distillationthe CH2Cl2 was distilled off under reduced pressure
  8. additionThe residue was added on a column of silica gel
  9. washthe fractions eluted with CH2Cl2
  10. customAcOEt (10:1) were collected
  11. distillationto distill off the solvent under reduced pressure
  12. additionPetroleum ether was added to the residue

Sources & evidence

ORD record
ord-8973d59d8ffa4e8e8708d85759fd5b8c
Source dataset
uspto-grants-1984_07
Patent number
US04463172

Reaction notes

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