Sodium Bicarbonate → 2-(2-Formamidothiazol-4-yl)-2-(4-bromo-3-hydroxybenzyloxyimino)acetic acid

HRID 745388노트

반응식

HRID 745388 반응식
P(O)(O)(O)=O.[Br:6][C:7]1[CH:15]=[CH:14][C:10]([CH2:11][O:12][NH2:13])=[CH:9][C:8]=1[OH:16].C(=O)(O)[O-].[Na+].[CH:22]([NH:24][C:25]1[S:26][CH:27]=[C:28]([C:30](=O)[C:31]([OH:33])=[O:32])[N:29]=1)=[O:23]>O.C(O)C>[CH:22]([NH:24][C:25]1[S:26][CH:27]=[C:28]([C:30](=[N:13][O:12][CH2:11][C:10]2[CH:14]=[CH:15][C:7]([Br:6])=[C:8]([OH:16])[CH:9]=2)[C:31]([OH:33])=[O:32])[N:29]=1)=[O:23]

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 13116693(2-Formamido-1,3-thiazol-4-yl)(oxo)acetic acidHCID 236167634-Bromo-3-hydroxybenzyloxyamine phosphate

생성물 1

HCID 540633902-(2-Formamidothiazol-4-yl)-2-(4-bromo-3-hydroxybenzyloxyimino)acetic acid수율 74%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

The solution of 4-bromo-3-hydroxybenzyloxyamine phosphate (17.4 g.) in water (200 ml.) and ethanol (200 ml.) was stirred at room temperature and adjusted to pH 7.0 with sodium bicarbonate. 2-(2-Formamidothiazol-4-yl)glyoxylic acid (10.0 g.) was added to the solution and the resulting suspension was adjusted to pH 4.0 to 4.5. After stirring the solution at room temperature for 2 hours, ethanol was removed from the resultant solution in vacuo. Ethyl acetate was added to aqueous residue and adjusted to pH 2.5 with 10% hydrochloric acid. The ethyl acetate layer was separated, washed with water and dried over magnesium sulfate. The solution was concentrated in vacuo to give 2-(2-formamidothiazol-4-yl)-2-(4-bromo-3-hydroxybenzyloxyimino)acetic acid (syn isomer, 14.8 g.).

후처리

  1. customethanol was removed from the resultant solution in vacuo
  2. additionEthyl acetate was added to aqueous residue
  3. customThe ethyl acetate layer was separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solution was concentrated in vacuo

출처 및 근거

ORD 기록
ord-90648fa19c684a33b4f3f66968f21bc9
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04598147

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