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Ethyl Acetate → HCID 131718139, compound

HRID 1734271
Notes
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Reaction equation

HRID 1734271 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:27][O:28][CH3:29])[C:10]([NH:12][C@@H:13]2[C:25](=[O:26])[N:15]3[C:16]([C:22]([OH:24])=[O:23])=[C:17]([CH2:20]Cl)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2].[CH3:30][N:31]1[CH2:36][CH2:35][N:34]([C:37](=[O:46])[C:38]2[CH:43]=[CH:42][C:41]([OH:44])=[C:40]([OH:45])[CH:39]=2)[CH2:33][CH2:32]1.C(OCC)(=O)C>CN(C)C=O>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:27][O:28][CH3:29])[C:10]([NH:12][C@@H:13]2[C:25](=[O:26])[N:15]3[C:16]([C:22]([O-:24])=[O:23])=[C:17]([CH2:20][N+:31]4([CH3:30])[CH2:36][CH2:35][N:34]([C:37](=[O:46])[C:38]5[CH:43]=[CH:42][C:41]([OH:44])=[C:40]([OH:45])[CH:39]=5)[CH2:33][CH2:32]4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 3062451Piperazine, 1-(3,4-dihydroxybenzoyl)-4-methyl-HCID 1317181417beta-[2-(2-Formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid

Product 1

HCID 131718139HCID 131718139, compoundYield 115.9%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7β-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid (syn isomer) (920 mg) in N,N-dimethylformamide (5 ml) was added 1-methyl-4-(3,4-dihydroxybenzoyl)piperazine (945 mg) at 0° C. and the mixture was stirred at 0° C. for 3.5 hours. The mixture was added dropwise to ethyl acetate (200 ml) under stirring and the pulverized product was collected by filtration and washed with ethyl acetate to give 7β-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-[1-methyl-4-(3,4-dihydroxybenzoyl)-1-piperazinio]methyl-3-cephem-4-carboxylate (syn isomer) (1.53 g).

Workup

  1. stirringunder stirring
  2. filtrationthe pulverized product was collected by filtration
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-a21126c5dc3d44038842991e32dcd14d
Source dataset
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05532354

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes