Hydrochloric Acid → HCID 131712232, compound
Reaction equation
[CH2:1]([O:3][N:4]=[C:5]([C:28]1[N:33]=[C:32]([NH:34]C=O)[CH:31]=[CH:30][N:29]=1)[C:6]([NH:8][CH:9]1[C:26](=[O:27])[N:11]2[C:12]([C:23]([OH:25])=[O:24])=[C:13]([CH2:16][S:17][C:18]3[S:19][CH:20]=[N:21][N:22]=3)[CH2:14][S:15][C@H:10]12)=[O:7])[CH3:2].Cl>>[NH2:34][C:32]1[CH:31]=[CH:30][N:29]=[C:28]([C:5](=[N:4][O:3][CH2:1][CH3:2])[C:6]([NH:8][CH:9]2[C:26](=[O:27])[N:11]3[C:12]([C:23]([OH:25])=[O:24])=[C:13]([CH2:16][S:17][C:18]4[S:19][CH:20]=[N:21][N:22]=4)[CH2:14][S:15][C@H:10]23)=[O:7])[N:33]=1Participants
Procedure
A solution of 7-[2-ethoxyimino-2-(4-formamidopyrimidin-2-yl)acetamido]-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (syn isomer) (3.97 g) and concentrated hydrochloric acid (0.73 ml) in methenol (80 ml) was stirred for 1.5 hours at ambient temperature. The solvent was evaporated to dryness and the residue was dissolved in water (100 ml). The aqueous solution was washed with ethyl acetate and adjusted to pH 3 with an aqueous solution of sodium bicarbonate and then subjected to column chromatography over nonionic adsorption resin, "Diaion HP 20". The column was washed with water and eluted with 50% aqueous methanol. The eluent containing a desired compound was evaporated to remove the methanol and then lyophilized to give 7-[2-(4-aminopyrimidin-2-yl)-2-ethoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (syn isomer) (1.75 g), mp 155°-160° C. (dec.).
Workup
- customThe solvent was evaporated to dryness
- dissolutionthe residue was dissolved in water (100 ml)
- washThe aqueous solution was washed with ethyl acetate
- washThe column was washed with water
- washeluted with 50% aqueous methanol
- additionThe eluent containing a desired compound
- customwas evaporated
- customto remove the methanol
Sources & evidence
- ORD record
- ord-3c8aa07533a24598a827005515908e2a
- Source dataset
- uspto-grants-1986_06
- Patent number
- US04596869
Reaction notes
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