Methanol → HCID 67894757, compound

HRID 1731701Notes

Reaction equation

HRID 1731701 reaction equation
N1C=CC=CC=1.C1(CC([NH:16][CH:17]2[C:39](=[O:40])[N:19]3[C:20]([C:26]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=4)=[O:27])=[C:21]([CH2:24][Cl:25])[CH2:22][S:23][C@H:18]23)=O)C=CC=CC=1.CO.O>C(Cl)Cl>[ClH:25].[NH2:16][CH:17]1[C:39](=[O:40])[N:19]2[C:20]([C:26]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=3)=[O:27])=[C:21]([CH2:24][Cl:25])[CH2:22][S:23][C@H:18]12

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1049PyridineHCID 67894858HCID 67894858, compound

Product 1

HCID 67894757HCID 67894757, compoundYield 166.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of phorphorus pentachloride (624 mg) in methylene chloride (15 ml) was added pyridine (0.242 ml) at -20° C. After the mixture was stirred for 20 minutes at the same temperature, p-nitrobenzyl 7-(2-phenylacetamido)-3-chloromethyl-3-cephem-4-carboxylate (502 mg) was added to the mixture at -20° C. The mixture was stirred for 30 minutes under ice-cooling. To the mixture was added methanol (0.65 ml) at -20° C., and the mixture was stirred for an hour at -20°~-5° C. Water (0.7 ml) was added thereto under ice-cooling. The mixture was stirred for an hour at the same temperature to give a precipitate. The precipitate was collected, washed with methylene chloride, water and diisopropyl ether successively and dried over phosphorus pentoxide to give p-nitrobenzyl 7-amino-3-chloromethyl-3-cephem-4-carboxylate monohydrochloride (0.35 g).

Workup

  1. additionwas added to the mixture at -20° C
  2. temperaturecooling
  3. stirringthe mixture was stirred for an hour at -20°~-5° C
  4. temperatureunder ice-cooling
  5. stirringThe mixture was stirred for an hour at the same temperature
  6. customto give a precipitate
  7. customThe precipitate was collected
  8. washwashed with methylene chloride, water and diisopropyl ether successively
  9. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-385f3a675fd945aaa164f70d5ce6b17f
Source dataset
uspto-grants-1986_11
Patent number
US04622318

Reaction notes

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