Methanol → HCID 131718062, compound

HRID 2253995Notes

Reaction equation

HRID 2253995 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.N1C=CC=CC=1.C1(CC([NH:22][C@@H: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[CH:36]=[CH:35][S:34][N:33]=4)[CH2:28][S:29][C@H:24]23)=O)C=CC=CC=1.CO>C(Cl)Cl>[NH2:22][C@@H: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[CH:36]=[CH:35][S:34][N:33]=3)[CH2:28][S:29][C@H:24]12

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 131718061HCID 131718061, compound

Product 1

HCID 131718062HCID 131718062, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

In 13 ml of methylene chloride were dissolved 913 mg of phosphorus pentachloride and 1.18 ml of pyridine, and 800 mg (1.46 mmol) of p-methoxybenzyl 7β-phenylacetamido-3-[2-(isothiazol-3-yl)vinyl]-3-cephem-4-carboxylate with 3.2 ml of methylene chloride were added therein at -30° C. After stirring for 3 hrs. under ice-cooling, the reaction solution was added to 13 ml of methanol at -30° C. After stirring for 1 hr. at the room temperature, the reaction solution was added to 30 ml of saturated saline solution and 30 ml of methylene chloride under ice-cooling, and stirred for 1 hr. as it was. The reaction solution was separated, and the aqueous layer was further extracted with 20 ml of methylene chloride. The layers of methylene chloride were combined, washed with saturated sodium hydrogen carbonate aqueous solution, and dried over anhydrous magnesium sulfate, and then, the solvent was evaporated off to give 1.15 g of a caramel. The caramel was column chromatographed on silica gel by eluting with chloroform-ethyl acetate to give 600 mg of p-methoxybenzyl 7β-amino-3-[2-(isothiazol-3yl)vinyl]-3-cephem-4-carboxylate.

Workup

  1. additionwere added
  2. customat -30° C
  3. temperatureunder ice-cooling
  4. stirringAfter stirring for 1 hr
  5. temperaturecooling
  6. stirringstirred for 1 hr
  7. customThe reaction solution was separated
  8. extractionthe aqueous layer was further extracted with 20 ml of methylene chloride
  9. washwashed with saturated sodium hydrogen carbonate aqueous solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customthe solvent was evaporated off
  12. customto give 1.15 g of a caramel
  13. customchromatographed on silica gel
  14. washby eluting with chloroform-ethyl acetate

Sources & evidence

ORD record
ord-f7f080c19a9d4c7e99406c55728cc90b
Source dataset
uspto-grants-1993_08
Patent number
US05233035

Reaction notes

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