Anisole → (Z)-2-((((5-Amino-1,2,4-thiadiazol-3-yl)(carboxy)methylene)amino)oxy)-2-methylpropanoic acid

HRID 373434노트

반응식

HRID 373434 반응식
[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:11]/[O:12][C:13]([C:16]([O:18]C(C)(C)C)=[O:17])([CH3:15])[CH3:14])/[C:8]([OH:10])=[O:9])[N:3]=1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:11]/[O:12][C:13]([C:16]([OH:18])=[O:17])([CH3:15])[CH3:14])/[C:8]([OH:10])=[O:9])[N:3]=1

참가 물질

4

반응물 2

HCID 7519AnisoleHCID 13577059(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(2-methyl-1-((2-methylpropan-2-yl)oxy)-1-oxopropan-2-yl)oxyiminoacetic acid

생성물 1

HCID 15077653(Z)-2-((((5-Amino-1,2,4-thiadiazol-3-yl)(carboxy)methylene)amino)oxy)-2-methylpropanoic acid수율 88%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

A solution of (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)acetic acid (17.8 g) and anisole (18 ml) in trifluoroacetic acid (36 ml) was stirred for 4.0 hours at room temperature. The reaction mixture was concentrated under reduced pressure and an aqueous solution of sodium bicarbonate was added thereto to adjust to pH 6.0. The aqueous solution was washed with ethyl acetate, adjusted to pH 3.8 with 6N hydrochloric acid and washed with ethyl acetate. The aqueous layer was separated and 6N hydrochloric acid was added thereto to adjust to pH 1.0. After the mixture was stirred for 10 minutes, the resultant precipitate was collected by filtration to give (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetic acid (13.0 g).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionan aqueous solution of sodium bicarbonate was added
  3. washThe aqueous solution was washed with ethyl acetate
  4. washwashed with ethyl acetate
  5. customThe aqueous layer was separated
  6. addition6N hydrochloric acid was added
  7. filtrationthe resultant precipitate was collected by filtration

출처 및 근거

ORD 기록
ord-62be96d0da894fb3a11fd12c8a63bbc0
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05162520

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