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Acetate → (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(3S)-2-oxopyrrolidin-3-yl]oxyiminoacetic acid

HRID 414793
Notes
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Reaction equation

HRID 414793 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]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 175AcetateHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13536831ethyl (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(3S)-2-oxopyrrolidin-3-yl]oxyiminoacetate

Product 1

HCID 13536828(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(3S)-2-oxopyrrolidin-3-yl]oxyiminoacetic acid

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 962WaterSolvent

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

  1. additionis added
  2. dissolutionto dissolve
  3. concentrationthe aqueous mixture is concentrated under reduced pressure
  4. customto remove methanol
  5. temperaturecooled
  6. customCrystalline precipitates
  7. filtrationare collected by filtration
  8. washthe crystals are washed with methanol
  9. customdried

Sources & evidence

ORD record
ord-fc7d7d995977475aa0ef831c8c76798a
Source dataset
uspto-grants-1988_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04794186

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes