Sodium Hydroxide → HCID 56637930, compound

HRID 414797Notes

Reaction equation

HRID 414797 reaction equation
[Cl:1][C:2]([Cl:28])([Cl:27])[CH2:3][O:4][C:5]([NH:7][C:8]1[S:9][CH:10]=[C:11](/[C:13](=[N:19]/[O:20][CH:21]2[CH2:25][CH2:24][NH:23][C:22]2=[O:26])/[C:14]([O:16]CC)=[O:15])[N:12]=1)=[O:6].[OH-].[Na+]>CO>[Cl:28][C:2]([Cl:1])([Cl:27])[CH2:3][O:4][C:5]([NH:7][C:8]1[S:9][CH:10]=[C:11]([C:13](=[N:19][O:20][CH:21]2[CH2:25][CH2:24][NH:23][C:22]2=[O:26])[C:14]([OH:16])=[O:15])[N:12]=1)=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13536855HCID 13536855, compound

Product 1

HCID 56637930HCID 56637930, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.42 g of ethyl (Z)-2-[2-(2,2,2-trichloroethoxycarbonylamino)thiazol-4-yl]-2-[(2-pyrrolidon-3-yl)oxyimino]acetate are suspended in 30 ml of methanol, and 3 ml of 2N sodium hydroxide are added thereto with ice-cooling. The mixture is stirred at room temperature for one hour and then refluxed for 30 minutes with heating. Then, the mixture is concentrated under reduced pressure to dryness. 5 ml of water are added to the residue, and the aqueous mixture is washed with ethyl acetate. The aqueous mixture is adjusted to pH 2 to 3 with diluted hydrochloric acid, and the mixture is extracted with a mixture of ethyl acetate and tetrahydrofuran (2:1). The extract is dried and concentrated under reduced pressure to dryness. The residue is purified by silica gel chromatography (solvent, ethyl acetate:methanol=4:1). 0.4 g of (Z)-2-[(2-(2,2,2-trichloroethoxycarbonyl-amino)thiazol-4-yl]-2-[(2-pyrrolidon-3-yl)oxyimino]acetic acid is obtained. This product begins to gradually decompose at 190° C.

Workup

  1. temperaturewith ice-cooling
  2. temperaturerefluxed for 30 minutes
  3. temperaturewith heating
  4. concentrationThen, the mixture is concentrated under reduced pressure to dryness
  5. addition5 ml of water are added to the residue
  6. washthe aqueous mixture is washed with ethyl acetate
  7. extractionthe mixture is extracted with a mixture of ethyl acetate and tetrahydrofuran (2:1)
  8. customThe extract is dried
  9. concentrationconcentrated under reduced pressure to dryness
  10. customThe residue is purified by silica gel chromatography (solvent, ethyl acetate:methanol=4:1)

Sources & evidence

ORD record
ord-d67c8e136bdd423487cfcdbd4342da01
Source dataset
uspto-grants-1988_12
Patent number
US04794186

Reaction notes

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