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Methanol → HCID 178477374, compound

HRID 1165945
Notes
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Reaction equation

HRID 1165945 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.N1C=CC=CC=1.[CH:13]([O:26][C:27]([C:29]1[N:34]2[C:35](=[O:46])[C@@H:36]([NH:37]C(=O)CC3SC=CC=3)[C@H:33]2[S:32][CH2:31][C:30]=1[CH:47]([S:49][C:50]1[NH:54][N:53]=[N:52][N:51]=1)[CH3:48])=[O:28])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CO>C(Cl)Cl.O>[CH:13]([O:26][C:27]([C:29]1[N:34]2[C:35](=[O:46])[CH:36]([NH2:37])[C@H:33]2[S:32][CH2:31][C:30]=1[CH:47]([S:49][C:50]1[NH:54][N:53]=[N:52][N:51]=1)[CH3:48])=[O:28])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 178477370HCID 178477370, compound

Product 1

HCID 178477374HCID 178477374, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-10 °C

Procedure

To a suspension of 6.25 g of phosphorus pentachloride in 45 ml of anhydrous methylene chloride cooled at -10° C., is added 20 ml of anhydrous methylene chloride solution containing 2.4 g of pyridine and the mixed solution is stirred for 30 minutes. To the solution is dropwise added a solution of 9.3 g of 7β-(2-thienylacetamido)-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid benzhydryl ester in 30 ml of anhydrous methylene chloride during 30 minutes under stirring and keeping at -20° C.--10° C. The mixture is further stirred for 2 hours at the same temperature and then cooled to -30° C.--20° C., followed by adding dropwise 56 ml of methanol. Thus obtained solution is stirred for 30 minutes, keeping the temperature of the solution between -5° C. and 5° C., and 60 ml of water is added dropwise thereto, followed by further stirring for 30 minutes. Methylene chloride layer is washed with saturated aq. NaCl solution and concentrated. To the concentrate is added a mixture of water and ethyl acetate under stirring to give 4.746 g of 7-amino-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid benzhydryl ester as a crystal. Yield 64.0%.

Workup

  1. stirringunder stirring
  2. customkeeping at -20° C.--10° C
  3. stirringThe mixture is further stirred for 2 hours at the same temperature
  4. temperaturecooled to -30° C.--20° C.
  5. stirringThus obtained solution is stirred for 30 minutes
  6. additionis added dropwise
  7. stirringby further stirring for 30 minutes
  8. washMethylene chloride layer is washed with saturated aq. NaCl solution
  9. concentrationconcentrated
  10. additionTo the concentrate is added
  11. additiona mixture of water and ethyl acetate
  12. stirringunder stirring

Sources & evidence

ORD record
ord-0fc3129dafb7476783d2fcdfe58c4e10
Source dataset
uspto-grants-1990_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04912212

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes