7-Aminocephalosporanic acid → HCID 20390078, compound
Reaction equation
[CH3:1][C:2]([O:4][CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=[O:3].[C:19]1([S:25][CH2:26][S:27][CH2:28][C:29](Cl)=[O:30])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[C:2]([O:4][CH2:5][C:6]1[CH2:15][S:14][CH:9]2[N:8]([C:11](=[O:12])[CH:10]2[NH:13][C:29](=[O:30])[CH2:28][S:27][CH2:26][S:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:7]=1[C:16]([OH:18])=[O:17])(=[O:3])[CH3:1]Participants
3
Procedure
3.1 gms. of 7-aminocephalosporanic acid and 3.4 gms. of [[(phenylthio)methyl]thio]acetyl chloride are treated according to the procedure of Example 3 to obtain DL-3-[(acetyloxy)methyl]-7-[[[[(phenylthio)methyl] thio]acetyl]-amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid. For purification, this product is converted to its potassium salt with potassium ethyl hexanoate. The reaction mixture is acidified and extracted with ethyl acetate to obtain the purified free acid. This is dissolved in methylene chloride and petroleum ether is added to the solution. The product precipitates in amorphous solid form.
Sources & evidence
- ORD record
- ord-490d6e346e6e450693a3361c54ec9085
- Source dataset
- uspto-grants-1977_01
- Patent number
- US04003893
Reaction notes
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