Hydrochloric Acid → HCID 131713335, compound

HRID 569378Notes

Reaction equation

HRID 569378 reaction equation
[NH2:1][CH:2]([C:23]([OH:25])=[O:24])[CH2:3][CH2:4][CH2:5][C:6]([NH:8][CH:9]1[C:21](=[O:22])[N:11]2C(C([O-])=O)=[C:13](CO)[CH2:14][S:15][C@H:10]12)=[O:7].[Na+].Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29].[C:33](=[O:36])([O-])[O-].[K+].[K+].[C:39]1([C:45]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[N+]=[N-])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.Cl.[CH:55]([O:58][CH:59]([CH3:61])[CH3:60])([CH3:57])C.[OH2:62]>CC(C)=O.C(OCC)(=O)C>[CH:45]([O:25][C:23]([CH:2]([NH:1][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:3][CH2:4][CH2:5][C:6]([NH:8][CH:9]1[C:21](=[O:22])[N:11]2[C:57]([C:55]([O:58][CH:59]([C:60]3[CH:52]=[CH:53][CH:48]=[CH:49][CH:50]=3)[C:61]3[CH:43]=[CH:44][CH:39]=[CH:40][CH:41]=3)=[O:62])=[C:33]([OH:36])[CH:14]([CH3:13])[S:15][C@H:10]12)=[O:7])=[O:24])([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 962WaterHCID 7914Diisopropyl EtherHCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 23719879HCID 23719879, compound

Product 1

HCID 131713335HCID 131713335, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of sodium 7-(5-amino-5-carboxypentanamido)-3-hydroxymethyl-3-cephem-4-carboxylate (10 g) in water (50 ml) and acetone (30 ml) was added ethyl chloroformate (7.14 g), and the mixture was stirred at 7°-8° C. for 45 minutes while maintaining the pH value at 7.8-8 with 40% aqueous potassium carbonate. To the solution was added diphenyldiazomethane (14.7 g) in ethyl acetate (122 ml), and the mixture was stirred at ambient temperature for an hour while maintaining the pH value at 2.5 with 6N hydrochloric acid. The organic layer was separated, washed with an aqueous sodium chloride. The solution was evaporated to give a residue, which was dissolved in acetone (30 ml). To diisopropyl ether (300 ml) was added the resultant acetone solution, and the precipitates were collected by filtration to give benzhydryl 7-(5-benzhydryloxycarbonyl-5-ethoxycarbonylaminopentanamido)-3-hydroxy-methyl-3-cephem-4-carboxylate (18.15 g).

Workup

  1. stirringthe mixture was stirred at ambient temperature for an hour
  2. customThe organic layer was separated
  3. washwashed with an aqueous sodium chloride
  4. customThe solution was evaporated
  5. customto give a residue, which
  6. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-88293d8473e84f6bb2a76b5ddecef0bd
Source dataset
uspto-grants-1988_03
Patent number
US04731443

Reaction notes

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