Pyridine → HCID 14621694, compound

HRID 1461169Notes

Reaction equation

HRID 1461169 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.N1C=CC=CC=1.C1(CC([NH:22][CH:23]2[C:49](=[O:50])[N:25]3[C:26]([C:37]([O:39][CH2:40][C:41]4[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=4)=[O:38])=[C:27](/[CH:30]=[CH:31]\[C:32]4[N:33]=[N:34][S:35][CH:36]=4)[CH2:28][S:29][C@H:24]23)=O)C=CC=CC=1.C(=O)(O)[O-].[Na+]>O.CO.C(Cl)Cl>[NH2:22][CH:23]1[C:49](=[O:50])[N:25]2[C:26]([C:37]([O:39][CH2:40][C:41]3[CH:42]=[CH:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=3)=[O:38])=[C:27](/[CH:30]=[CH:31]\[C:32]3[N:33]=[N:34][S:35][CH:36]=3)[CH2:28][S:29][C@H:24]12

Participants

8

Reactant 4

HCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 67938783HCID 67938783, compound

Product 1

HCID 14621694HCID 14621694, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

Phosphorus pentachloride (8.12 g, 39 mmol) was added to methylene chloride (70 ml) and cooled to 5° C. It was stirred for 1 hour by addition of pyridine (10.39 g, 130 mmol). p-Methoxybenzyl 7-phenylacetamido-3-[(Z)-2-(1,2,3-thiadiazol-4-yl)vinyl]-3-cephem-4-carboxylate (7.27 g, 13 mmol) was added to this reaction solution and it was stirred at 5° C. for 4 hours. The reaction solution was cooled to -30° C. and stirred for 1 hour by addition of dehydrated methanol (53 ml). The temperature of the reaction solution was returned to -10° C. and it was stirred for 10 minutes by addition of water (10 ml). Saturated sodium bicarbonate was added to the reaction solution to adjust to pH 4, and then the solvent was distilled off under reduced pressure. The residue was extracted with ethyl acetate, then washed with water and dried over magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography thereby p-methoxybenzyl 7-amino-3-[(Z)-2-(1,2,3-thiadiazol-4-yl)vinyl]-3-cephem-4-carboxylate (3.9 g, 70% yield) was obtained as a light yellow powder substance.

Workup

  1. temperatureThe reaction solution was cooled to -30° C.
  2. customwas returned to -10° C.
  3. distillationthe solvent was distilled off under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off
  8. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-43e15cdca60049b3a4494949feeb505b
Source dataset
uspto-grants-1991_12
Patent number
US05073551

Reaction notes

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