2-Methyltetrahydrofuran → N-(2-(tert-Butyl)-5-hydroxy-4-(1-hydroxy-2-methylpropan-2-yl)phenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

HRID 76790

반응식

HRID 76790 반응식
[C:1]([C:5]1[C:6]([NH:17][C:18]([C:20]2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)=[O:19])=[CH:7][C:8]2[O:12][C:11](=[O:13])[C:10]([CH3:15])([CH3:14])[C:9]=2[CH:16]=1)([CH3:4])([CH3:3])[CH3:2].CC1OCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.OC(C(O)C([O-])=O)C([O-])=O.[Na+].[K+]>CC(OC)(C)C>[C:1]([C:5]1[CH:16]=[C:9]([C:10]([CH3:15])([CH3:14])[CH2:11][OH:13])[C:8]([OH:12])=[CH:7][C:6]=1[NH:17][C:18]([C:20]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1)=[O:19])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 73012-MethyltetrahydrofuranHCID 2724148Sodium potassium tartrate tetrahydrateHCID 21226445Aluminium lithium hydrideHCID 59544159N-(5-(tert-Butyl)-3,3-dimethyl-2-oxo-2,3-dihydrobenzofuran-6-yl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

생성물 1

HCID 46897962N-(2-(tert-Butyl)-5-hydroxy-4-(1-hydroxy-2-methylpropan-2-yl)phenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매

실험 절차

A 3-neck 50 mL round bottom flask was equipped with magnetic stirrer, nitrogen bubbler and thermocouple. Compound 21 (514 mg, 1.27 mmol) and 2-MeTHF (4 mL) are charged to the flask. The reaction mixture was stirred at room temperature. Lithium aluminum hydride (204 mg, 6.6 mmol) was added as solid until 100% conversion is achieved, which was monitored using HPLC. Potassium sodium 2,3-dihydroxybutanedioate tetrahydrate salt (50 mL of a 400 g/L solution) and MTBE (50 mL) were added to the reaction mixture. The resulting solution was stirred for 15 minutes and then let sit for 15 min. The organic layer was separated and the pH of the aqueous layer was adjusted to a pH of about 6-7 by adding Tartaric acid. The aqueous layer was extracted with MTBE. The organic layer was concentrated and dried under high vacuum to provide the title compound as an off-white powder. The 1H-NMR spectrum was consistent with that reported above.

후처리

  1. customA 3-neck 50 mL round bottom flask was equipped with magnetic stirrer
  2. stirringThe resulting solution was stirred for 15 minutes
  3. customThe organic layer was separated
  4. additionby adding Tartaric acid
  5. extractionThe aqueous layer was extracted with MTBE
  6. concentrationThe organic layer was concentrated
  7. customdried under high vacuum

출처 및 근거

ORD 기록
ord-272ab8a11a4b4c179978de74ad16a2e8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835639B2

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