Pyridine → Diphenylmethyl 3-methoxyiminomethyl-7-amino-3-cephem-4-carboxylate

HRID 972494Notes

Reaction equation

HRID 972494 reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH2:6][S:7][C@@H:8]2[CH:28]([NH:29]C(=O)CC3SC=CC=3)[C:27](=[O:38])[N:9]2[C:10]=1[C:11]([O:13][CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl>C1C=CC=CC=1.CO.O>[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH2:6][S:7][C@@H:8]2[CH:28]([NH2:29])[C:27](=[O:38])[N:9]2[C:10]=1[C:11]([O:13][CH:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:12]

Participants

7

Reactant 3

HCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 131710499Diphenylmethyl 3-methoxyiminomethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate

Product 1

HCID 131710500Diphenylmethyl 3-methoxyiminomethyl-7-amino-3-cephem-4-carboxylateYield 94.2%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent2×HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of diphenylmethyl 3-methoxyiminomethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate (887 mg) in benzene (48 ml) are added pyridine (0.26 ml) and phosphorous pentachloride (676 mg) in benzene (48 ml), and the mixture is stirred for 90 minutes. The mixture is diluted with methanol (96 ml), stirred for 2.5 hours, diluted with water (9.6 ml), stirred for 20 minutes, and evaporated at a temperature lower than 40° C. The residue is dissolved in ethyl acetate, washed with water, aqueous sodium hydrogen carbonate and water, dried and evaporated. The residue crystallizes from a mixture of ether and petroleum ether to give diphenylmethyl 3-methoxyiminomethyl-7-amino-3-cephem-4-carboxylate (639 mg; 94.2 %). m.p. 135°-145° C.

Workup

  1. stirringstirred for 2.5 hours
  2. stirringstirred for 20 minutes
  3. customevaporated at a temperature lower than 40° C
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washwashed with water, aqueous sodium hydrogen carbonate and water
  6. customdried
  7. customevaporated
  8. customThe residue crystallizes from a mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-189f7ad80a1b43bc9e80e7bf1384d66f
Source dataset
uspto-grants-1977_10
Patent number
US04053469

Reaction notes

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