Sodium Hydroxide → 6-Chloro-7-(4-(6-(3,4-dichlorophenyl)pyridin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylic acid

HRID 1626430노트

반응식

HRID 1626430 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:35])[NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=4)[N:22]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:36]([O:38]CC)=[O:37].[OH-].[Na+]>C1COCC1.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19](=[O:35])[NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=4)[N:22]=3)=[CH:17][CH:18]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:36]([OH:38])=[O:37]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 67286797Ethyl 6-chloro-7-(4-(6-(3,4-dichlorophenyl)pyridin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate

생성물 1

HCID 672889976-Chloro-7-(4-(6-(3,4-dichlorophenyl)pyridin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylic acid수율 66%

시약·촉매·용매 1

HCID 21873804Tetrahydrofuran ethanol용매

실험 절차

To a solution of ethyl 6-chloro-7-(4-(6-(3,4-dichlorophenyl)pyridin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate (0.051 g, 0.085 mmol) in 3:1 v/v THF/ethanol (1 ml) was added 1M sodium hydroxide (0.20 ml, 0.20 mmol), and the reaction was stirred for 16 hours. The reaction was concentrated, taken up in water, and acidified with 1M hydrochloric acid. The reaction was extracted twice with EtOAc, and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated. The crude material was purified by silica gel preparative thin-layer chromatography, eluting with 95:5:1 DCM/MeOH/glacial acetic acid to yield the desired compound (0.032 g, 0.056 mmol, 66% yield). MS (apci) m/z=569.0 (M+H).

후처리

  1. concentrationThe reaction was concentrated
  2. extractionThe reaction was extracted twice with EtOAc
  3. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by silica gel preparative thin-layer chromatography
  7. washeluting with 95:5:1 DCM/MeOH/glacial acetic acid

출처 및 근거

ORD 기록
ord-592b901e88f84668ac1b5e7e31cae60c
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785445B2

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