Ethyl Acetate → HCID 131718139, compound

HRID 1609671Notes

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]

Participants

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

custom5 hours
stirringunder stirring
filtrationthe pulverized product was collected by filtration
washwashed with ethyl acetate

Sources & evidence

ORD record: ord-cfffe8f59a8643b297e6216d87a35959
Source dataset: uspto-grants-1995_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05401734

Reaction notes

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