Formic Acid → HCID 88523025, compound
Reaction equation
C([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:63]/[O:64]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)/[C:27]([NH:29][CH:30]2[C:61](=[O:62])[N:32]3[C:33]([C:45]([O:47]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:46])=[C:34](/[CH:37]=[CH:38]\[C:39]4[N:40]=[N:41][S:42][C:43]=4[CH3:44])[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)=O.Cl.C(=O)(O)[O-].[Na+:92]>>[NH2:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:63]/[OH:64])/[C:27]([NH:29][CH:30]2[C:61](=[O:62])[N:32]3[C:33]([C:45]([O-:47])=[O:46])=[C:34](/[CH:37]=[CH:38]\[C:39]4[N:40]=[N:41][S:42][C:43]=4[CH3:44])[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1.[Na+:92]Participants
Procedure
Benzhydryl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(Z)-2-(5-methyl-1,2,3-thiadiazol-4-yl)vinyl]-3-cephem-4-carboxylate (0.5 g, 0.4 mmol) was stirred at room temperature for 2 hours by addition of formic acid (5 ml). Concentrated hydrochloric acid (40 μl) was added to the reaction solution and it was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure and then the residue was cleansed with ether thereby a powdered product was obtained. This one was dissolved in aqueous sodium bicarbonate solution and purified by HP-20 column chromatography thereby sodium 7-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-[(Z)-2-(5-methyl-1,2,3-thiadiazol-4-yl)vinyl]-3-cephem-4-carboxylate (0.13 g) was obtained.
Workup
- concentrationThe reaction solution was concentrated under reduced pressure
- customa powdered product was obtained
- custompurified by HP-20 column chromatography
Sources & evidence
- ORD record
- ord-f67fb7c7a9c240ce9ba37d78d0662e8e
- Source dataset
- uspto-grants-1991_12
- Patent number
- US05073551
Reaction notes
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