2-Aminothiophenol → 2-(3-(Benzo[d]thiazol-2-yl)phenoxy)-2-methylpropanoic acid

HRID 1748998노트

반응식

HRID 1748998 반응식
[CH:1]([C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[O:6][C:7]([CH3:14])([CH3:13])[C:8]([O:10]CC)=[O:9])=O.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[SH:25].[OH-].[Na+]>CO>[S:25]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[C:1]1[C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[O:6][C:7]([CH3:13])([CH3:14])[C:8]([OH:10])=[O:9]

참가 물질

5

반응물 3

HCID 87132-AminothiophenolHCID 14798Sodium HydroxideHCID 18766496Ethyl 2-(3-formylphenoxy)-2-methylpropanoate

생성물 1

HCID 682792962-(3-(Benzo[d]thiazol-2-yl)phenoxy)-2-methylpropanoic acid수율 67.7%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

In a methanol solvent, a solution including Compound 97b (1.0 eq.) and 2-aminothiophenol (1.0 eq.) was stirred at room temperature for 22 hours. After methanol was evaporated, the residual was purified by silica gel column chromatography using hexane and ethyl acetate (14:1) as a developer. The obtained product was dissolved with 1,4-dioxane, and then, 1 N NaOH (1.5 eq.) was added thereto. The reaction mixture was stirred at room temperature for 17 hours, and 1,4-dioxane was evaporated. The reaction mixture was stirred at room temperature for 17 hours, and 1,4-dioxane was evaporated therefrom. The residual was distributed between ethyl acetate and water, an aqueous layer was acidified with 6 N HCl. The produced precipitate was filtered and washed with water to obtain Compound 120.

후처리

  1. customAfter methanol was evaporated
  2. customthe residual was purified by silica gel column chromatography
  3. dissolutionThe obtained product was dissolved with 1,4-dioxane
  4. stirringThe reaction mixture was stirred at room temperature for 17 hours
  5. custom1,4-dioxane was evaporated
  6. stirringThe reaction mixture was stirred at room temperature for 17 hours
  7. custom1,4-dioxane was evaporated
  8. filtrationThe produced precipitate was filtered
  9. washwashed with water

출처 및 근거

ORD 기록
ord-0893179ebb1f423a8084b94bb86faae8
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09155690B2

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