Pyridine → HCID 131716167, compound

HRID 2351152Notes

Reaction equation

HRID 2351152 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.N1C=CC=CC=1.C1(CC([NH:22][CH:23]2[C:45](=[O:46])[N:25]3[C:26]([C:32]([O:34][CH2:35][C:36]4[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=4)=[S:33])=[C:27]([CH:30]=[CH2:31])[CH2:28][S:29][C@H:24]23)=O)C=CC=CC=1.C(OC(C)C)(C)C>C(Cl)Cl.O.CO>[NH2:22][CH:23]1[C:45](=[O:46])[N:25]2[C:26]([C:32]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=3)=[S:33])=[C:27]([CH:30]=[CH2:31])[CH2:28][S:29][C@H:24]12

Participants

8

Reactant 4

HCID 1049PyridineHCID 7914Diisopropyl EtherHCID 24819Phosphorus pentachlorideHCID 131716168HCID 131716168, compound

Product 1

HCID 131716167HCID 131716167, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of phosphorus pentachloride (366 mg) in methylene chloride (6ml) was added pyridine (0.142 ml) at -30° C. After the mixture was stirred for 30 minutes at the same temperature, p-nitrobenzyl 7-(2-phenylacetamido)-3-vinylthio-3-cephem-4-carboxylate (300 mg) was added thereto at -30° C. The mixture was stirred for 1 hour under the ice-cooling to the mixture was added methanol (0.38 ml) at -30° C., and the mixture was stirred for 2 hours at -15 ~-20° C. Water (0.4 ml) was added thereto under ice-cooling. Diisopropyl ether (5 ml) was added to the mixture to give a precipitate. The precipitate was collected, washed with water and diisopropyl ether successively and dried over phosphorus pentoxide to give p-nitrobenzyl 7-amino-3-vinylthio-3-cephem-4-carboxylate hdrochloride (181 mg).

Workup

  1. additionwas added
  2. customat -30° C
  3. temperaturecooling to the mixture
  4. temperatureunder ice-cooling
  5. customto give a precipitate
  6. customThe precipitate was collected
  7. washwashed with water and diisopropyl ether successively
  8. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-e19839d8541f4f7285f7907b4cdf1336
Source dataset
uspto-grants-1989_10
Patent number
US04871730

Reaction notes

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