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Sodium Hydroxide → (2Z)-2-(2-acetamido-1,3-thiazol-4-yl)-2-(2-oxopyrrolidin-3-yl)oxyiminoacetic acid

HRID 414796
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HRID 414796 반응식
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8](/[C:10](=[N:16]/[O:17][CH:18]2[CH2:22][CH2:21][NH:20][C:19]2=[O:23])/[C:11]([O:13]CC)=[O:12])[N:9]=1)(=[O:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8](/[C:10](=[N:16]/[O:17][CH:18]2[CH2:22][CH2:21][NH:20][C:19]2=[O:23])/[C:11]([OH:13])=[O:12])[N:9]=1)(=[O:3])[CH3:2]
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4

반응물 2

HCID 14798Sodium HydroxideHCID 13536846ethyl (2Z)-2-(2-acetamido-1,3-thiazol-4-yl)-2-(2-oxopyrrolidin-3-yl)oxyiminoacetate

생성물 1

HCID 13536843(2Z)-2-(2-acetamido-1,3-thiazol-4-yl)-2-(2-oxopyrrolidin-3-yl)oxyiminoacetic acid수율 51.3%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

1.7 g of ethyl (Z)-2-(2-acetamidothiazol-4-yl)-2-[(2-pyrrolidon-3-yl)oxyimino]acetate are suspended in 17 ml of methanol, and 5 ml of 2N sodium hydroxide are added thereto. The mixture is refluxed for 30 minutes with heating. Then, the mixture is concentrated under reduced pressure to remove methanol. The residue is adjusted to pH 2 with diluted hydrochloric acid, and the aqueous 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 crystallized with isopropanol, and the crystals are collected by filtration and then recrystallized from water. 0.8 g of (Z)-2-(2-acetamidothiazol-4-yl)-2-[(2-pyrrolidon-3-yl)oxyimino]acetic acid is obtained.

후처리

  1. temperatureThe mixture is refluxed for 30 minutes
  2. temperaturewith heating
  3. concentrationThen, the mixture is concentrated under reduced pressure
  4. customto remove methanol
  5. extractionthe aqueous mixture is extracted with a mixture of ethyl acetate and tetrahydrofuran (2:1)
  6. customThe extract is dried
  7. concentrationconcentrated under reduced pressure to dryness
  8. customThe residue is crystallized with isopropanol
  9. filtrationthe crystals are collected by filtration
  10. customrecrystallized from water

출처 및 근거

ORD 기록
ord-cd07c546c0d04566945510d319f30c09
출처 데이터셋
uspto-grants-1988_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04794186

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