Acetate → (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(3S)-2-oxopyrrolidin-3-yl]oxyiminoacetic acid
Reaction equation
[OH-].[Na+].C([O-])(=O)C.Cl.[NH2:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:20]/[O:21][C@H:22]2[CH2:26][CH2:25][NH:24][C:23]2=[O:27])/[C:15]([O:17]CC)=[O:16])[N:13]=1>CO.O>[NH2:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:20]/[O:21][C@H:22]2[CH2:26][CH2:25][NH:24][C:23]2=[O:27])/[C:15]([OH:17])=[O:16])[N:13]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
0.27 g of sodium hydroxide is dissolved in a mixture of 3 ml of methanol and one ml of water, and one g of ethyl (Z)-2-(2-aminothiazol-4-yl)-2-[((3S)-2-pyrrolidon-3yl)oxyimino]acetate is added thereto. The mixture is stirred at 20° C. for one hour to dissolve said acetate therein. The solution is adjusted to pH 5 with 10% hydrochloric acid, and the aqueous mixture is concentrated under reduced pressure to remove methanol. The residue is adjusted to pH 3 with 10% hydrochloric acid, and the aqueous mixture is ice-cooled. Crystalline precipitates are collected by filtration, and the crystals are washed with methanol and then dried. 730 mg of (Z)-2-(2-aminothiazol-4-yl)-2-[((3S)-2-pyrrolidon-3-yl)oxyimino]acetic acid are obtained.
Workup
- additionis added
- dissolutionto dissolve
- concentrationthe aqueous mixture is concentrated under reduced pressure
- customto remove methanol
- temperaturecooled
- customCrystalline precipitates
- filtrationare collected by filtration
- washthe crystals are washed with methanol
- customdried
Sources & evidence
- ORD record
- ord-fc7d7d995977475aa0ef831c8c76798a
- Source dataset
- uspto-grants-1988_12
- Patent number
- US04794186
Reaction notes
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