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Ethyl Acetate → 1-Propionyloxyethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

HRID 1463051
Notes
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Reaction equation

HRID 1463051 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:23][O:24][CH3:25])[C:8]([NH:10][CH:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C(=O)([O-])[O-].[K+].[K+].[C:32]([O:36][CH:37](Cl)[CH3:38])(=[O:35])[CH2:33][CH3:34].C(OCC)(=O)C>CS(C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:23][O:24][CH3:25])[C:8]([NH:10][CH:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([O:20][CH:37]([O:36][C:32](=[O:35])[CH2:33][CH3:34])[CH3:38])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 135066761-Chloroethyl propionateHCID 1317124447-[2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

Product 1

HCID 1317136041-Propionyloxyethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylateYield 63.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn-isomer, 100 g) in dimethylsulfoxide (650 ml) was added potassium carbonate (21.6 g). Thereto was added 1-chloroethyl propionate (42.8 g) at 40° C. and the mixture was stirred at the same temperature for 2 hours. The reaction mixture was poured into a mixture of ice-water (3 l) and ethyl acetate (2 l), and the separated organic layer was washed in turn with 5% aqueous sodium bicarbonate (300 ml×2), water (300 ml) and an aqueous sodium chloride, followed by drying over magnesium sulfate. After treating with activated charcoal, the solvent was removed by evaporation, and the residue was pulverized with diisopropyl ether to give 1-propionyloxyethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn-isomer, 80 g).

Workup

  1. washthe separated organic layer was washed in turn with 5% aqueous sodium bicarbonate (300 ml×2), water (300 ml)
  2. dry with materialby drying over magnesium sulfate
  3. additionAfter treating with activated charcoal
  4. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-aa1dd4350953410aac9900992e5093d3
Source dataset
uspto-grants-1984_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04463002

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes