Methanol → HCID 131713528, compound

HRID 1262753Notes

Reaction equation

HRID 1262753 reaction equation
N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)[Cl:8].C1(CC([NH:22][CH:23]2[C:47](=[O:48])[N:25]3[C:26]([C:31]([O:33][CH:34]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[S:32])=[C:27]([CH3:30])[CH2:28][S:29][C@H:24]23)=O)C=CC=CC=1.CO>C(Cl)Cl>[ClH:8].[NH2:22][CH:23]1[C:47](=[O:48])[N:25]2[C:26]([C:31]([O:33][CH:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[S:32])=[C:27]([CH3:30])[CH2:28][S:29][C@H:24]12

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 131713531HCID 131713531, compound

Product 1

HCID 131713528HCID 131713528, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of pyridine phosphorus pentachloride complex prepared from pyridine (20 g) and phosphorus pentachloride (52.5 g) in methylene chloride (860 ml) was added benzhydryl 7-phenylacetamido-3-methylthio-3-cephem-4-carboxylate (67.0 g) under ice-cooling with stirring. The mixture was stirred at the same temperature for 30 minutes, and poured into methanol (650 ml) at -30° C. The mixed solution was stirred at -5° to -15° C. for 10 minutes and then evaporated under reduced pressure. To the residue were added ethyl acetate (500 ml) and cooled water (500 ml). The mixture was stirred for several minutes. The crystalline materials were collected by filtration and washed with diethyl ether to give benzhydryl 7-amino-3-methylthio-3-cephem-4-carboxylate hydrochloride (36.1 g), mp. 170° to 171° C. (dec.).

Workup

  1. additionTo a suspension of pyridine phosphorus pentachloride complex
  2. temperaturecooling
  3. stirringThe mixture was stirred at the same temperature for 30 minutes
  4. stirringThe mixed solution was stirred at -5° to -15° C. for 10 minutes
  5. customevaporated under reduced pressure
  6. additionTo the residue were added ethyl acetate (500 ml)
  7. temperaturecooled water (500 ml)
  8. stirringThe mixture was stirred for several minutes
  9. filtrationThe crystalline materials were collected by filtration
  10. washwashed with diethyl ether

Sources & evidence

ORD record
ord-8a4a719088044b67817f7695591f9f37
Source dataset
uspto-grants-1984_06
Patent number
US04452851

Reaction notes

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