3,3,3-Trifluoropropionic acid → N-(4-chloro-3-methylisothiazol-5-yl)-2-[4-hydroxy-3-(3,3,3-trifluoropropionamido)phenyl]propionamide

HRID 48161

반응식

HRID 48161 반응식
[Cl:1][C:2]1[C:3]([CH3:20])=[N:4][S:5][C:6]=1[NH:7][C:8](=[O:19])[CH:9]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([NH2:18])[CH:12]=1)[CH3:10].[F:21][C:22]([F:28])([F:27])[CH2:23][C:24](O)=[O:25].Cl.C(N(CC)CCCN=C=NCC)C>CN(C)C(=O)C>[Cl:1][C:2]1[C:3]([CH3:20])=[N:4][S:5][C:6]=1[NH:7][C:8](=[O:19])[CH:9]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([NH:18][C:24](=[O:25])[CH2:23][C:22]([F:28])([F:27])[F:21])[CH:12]=1)[CH3:10]

참가 물질

5

반응물 3

HCID 27779723,3,3-Trifluoropropionic acidHCID 99645121-(3-Diethylaminopropyl)-3-ethylcarbodiimide hydrochlorideHCID 22742099N-(4-chloro-3-methylisothiazol-5-yl)-2-(3-amino-4-hydroxyphenyl)propionamide

생성물 1

HCID 22742118N-(4-chloro-3-methylisothiazol-5-yl)-2-[4-hydroxy-3-(3,3,3-trifluoropropionamido)phenyl]propionamide수율 73.5%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

A mixture of N-(4-chloro-3-methylisothiazol-5-yl)-2-(3-amino-4-hydroxyphenyl)propionamide (0.65 g, 0.002 mol), 3,3,3-trifluoropropionic acid (0.267 g, 0.002 mol) and 1-(3-diethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.40 g, 0.002 mol) was stirred in N,N-dimethylacetamide (8 ml) at room temperature for 7 hours and was then allowed to stand at room temperature overnight. The reaction was quenched with water and extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate:hexane 1:1, to give N-(4-chloro-3-methylisothiazol-5-yl)-2-[4-hydroxy-3-(3,3,3-trifluoropropionamido)phenyl]propionamide (0.62 g) as a white solid.

후처리

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate was evaporated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel
  9. washeluting with ethyl acetate:hexane 1:1

출처 및 근거

ORD 기록
ord-4c9a56a369914b5eb3b3ecfbd160c61f
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703347B2

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