Phosphoric Acid → HCID 131713618, compound

HRID 1463149Notes

Reaction equation

HRID 1463149 reaction equation
S1C=CC=C1CC([NH:9][CH:10]1[C:38](=[O:39])[N:12]2[C:13]([C:22]([O:24][CH:25]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])=[C:14]([CH:18]=[N:19][O:20][CH3:21])[C@@H:15]([CH3:17])[S:16][C@H:11]12)=O.P(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:38](=[O:39])[N:12]2[C:13]([C:22]([O:24][CH:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[O:23])=[C:14]([CH:18]=[N:19][O:20][CH3:21])[C@@H:15]([CH3:17])[S:16][C@H:11]12

Participants

8

Reactant 4

HCID 1004Phosphoric AcidHCID 24387Phosphorus trichlorideHCID 24450Potassium Phosphate, DibasicHCID 131713619HCID 131713619, compound

Product 1

HCID 131713618HCID 131713618, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A 5 ml portion of pyridine was added to a solution of 2.8 g of diphenylmethy 7-(2-thienylacetamido)-2α-methyl-3-methoxyiminomethylceph-3-em-4-carboxylate in 60 ml of CH2Cl2, and 3.05 g of PCl3 was then added to the mixture at -10° C. under a stream of nitrogen, followed by stirring at the same temperature for 1 hour. After adding 50 ml of MeOH in once, the mixture was stirred at from -15° to -10° C. for 30 minutes and further at room temperature for 2 hours. Following addition of 100 ml of 0.5M K2HPO4 solution, the reaction solution was adjusted to pH 2.0 with 25% H3PO4, and stirred for 30 minutes to separate out the CH2Cl2 layer. The CH2Cl2 layer was washed with saturated aqueous NaCl solution, and dried over MgSO4 , followed by distilling off the CH2Cl2 under reduced pressure. The residue was added on a column of silica gel, and the fractions eluted with CH2Cl2.AcOEt (35:1) were collected to distill off the solvent under reduce pressure, thus yielding 1.44 g (66%) of diphenylmethyl 7-amino-2α-methyl-3-methoxyiminomethylceph-3-em-4-carboxylate.

Workup

  1. additionwas then added to the mixture at -10° C. under a stream of nitrogen
  2. stirringwas stirred at from -15° to -10° C. for 30 minutes and further at room temperature for 2 hours
  3. stirringstirred for 30 minutes
  4. customto separate out the CH2Cl2 layer
  5. washThe CH2Cl2 layer was washed with saturated aqueous NaCl solution
  6. dry with materialdried over MgSO4
  7. distillationby distilling off the CH2Cl2 under reduced pressure
  8. additionThe residue was added on a column of silica gel
  9. washthe fractions eluted with CH2Cl2
  10. customAcOEt (35:1) were collected
  11. distillationto distill off the solvent

Sources & evidence

ORD record
ord-7509bb59575f4329b264935fe8dafe74
Source dataset
uspto-grants-1984_07
Patent number
US04463172

Reaction notes

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