Pyridine → HCID 131716354, compound

HRID 2073478Notes

Reaction equation

HRID 2073478 reaction equation
C1(CC([NH:10][CH:11]2[C:42](=[O:43])[N:13]3[C:14]([C:26]([O:28][CH:29]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:27])=[C:15]([CH:18]=[CH:19][C:20]4[S:24][CH:23]=[N:22][C:21]=4[CH3:25])[CH2:16][S:17][C@H:12]23)=O)C=CC=CC=1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(Cl)Cl.O.CO>[NH2:10][CH:11]1[C:42](=[O:43])[N:13]2[C:14]([C:26]([O:28][CH:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[O:27])=[C:15]([CH:18]=[CH:19][C:20]3[S:24][CH:23]=[N:22][C:21]=3[CH3:25])[CH2:16][S:17][C@H:12]12

Participants

8

Reactant 4

HCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 131716355HCID 131716355, compound

Product 1

HCID 131716354HCID 131716354, compoundYield 54.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

In 40 ml of methylene chloride was dissolved the diphenylmethyl 7-phenylacetamido-3-[2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylate (3.04 g, 5 mmoles) obtained as above. The resultant solution was cooled down to -20° C. After adding pyridine (1.62 ml) and phosphorus pentachloride (2.08 g), the resultant mixture was stirred at 5° C. for 3 hours and then cooled again to -20° C. After a prompt addition of 4 ml of methanol, the resultant mixture was stirred at 20° C. for 2 hours. The reaction mixture was then cooled to -10° C., followed by addition of 20 ml of chilled water. The mixture obtained was agitated vigorously. An aqueous solution of sodium bicarbonate was added to the mixture to adjust its pH to 2.0. The organic layer was then separated, followed by its washing with an aqueous solution of sodium bicarbonate and then with saline. The organic solution was then dried magnesium sulfate and the solvent was distilled off under reduced pressure. Ethyl acetate (10 ml) was added to the residue and the resultant mixture was allowed to stand overnight in an ice box. Deposited crystals were collected by filtration, washed with ethyl acetate and then dried under reduced pressure, to give 1.34 g of diphenylmethyl 7-amino-3-[2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4carboxylate as yellow powder (yield: 54%).

Workup

  1. customobtained as above
  2. temperatureThe reaction mixture was then cooled to -10° C.
  3. customThe mixture obtained
  4. customThe organic layer was then separated
  5. washwashing with an aqueous solution of sodium bicarbonate
  6. distillationdried magnesium sulfate and the solvent was distilled off under reduced pressure
  7. additionEthyl acetate (10 ml) was added to the residue
  8. filtrationDeposited crystals were collected by filtration
  9. washwashed with ethyl acetate
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-a11904cc69294afc810d14a3b4b82efb
Source dataset
uspto-grants-1990_04
Patent number
US04918068

Reaction notes

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