Triethylamine → 2-methyl-2-(methylsulfonyl)-4-(4-phenoxyphenyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

HRID 533549노트

반응식

HRID 533549 반응식
[CH3:1][C:2]([S:21]([CH3:24])(=[O:23])=[O:22])([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)[C:3](O)=[O:4].O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[O:43]1[CH2:48][CH2:47][CH2:46][CH2:45][CH:44]1[O:49][NH2:50]>C(Cl)Cl.O>[CH3:1][C:2]([S:21]([CH3:24])(=[O:23])=[O:22])([CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)[C:3]([NH:50][O:49][CH:44]1[CH2:45][CH2:46][CH2:47][CH2:48][O:43]1)=[O:4]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 665779192-Methyl-2-(methylsulfonyl)-4-(4-phenoxyphenyl)butanoic acid

생성물 1

HCID 866687712-methyl-2-(methylsulfonyl)-4-(4-phenoxyphenyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2-methyl-2-(methylsulfonyl)-4-(4-phenoxyphenyl)butanoic acid (285 mg, 0.818 mmol) in methylene chloride (8.18 mL) at ambient temperature was added 1,(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (220 mg, 1.1 mmol), 1-hydroxy benzotriazole monohydrate (230 mg, 1.5 mmol), triethylamine (0.2 mL, 1.4 mmol) and O-tetrahydro-2H-pyran-2-yl-hydroxylamine (140 mg, 1.2 mmol). The resulting mixture was stirred at ambient temperature overnight. The mixture was diluted with methylene chloride and water. The phases were separated and the aqueous layer extracted with methylene chloride two times. The organic extracts were combined and dried over magnesium sulfate, filtered and concentrated in vacuo to a crude residue. The crude residue was purified via silica gel chromatography eluting with methylene chloride and methanol. The fractions containing the desired product were combined and concentrated in vacuo to afford 2-methyl-2-(methylsulfonyl)-4-(4-phenoxyphenyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide as a solid. 247.2 mg

후처리

  1. customThe phases were separated
  2. extractionthe aqueous layer extracted with methylene chloride two times
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a crude residue
  6. customThe crude residue was purified via silica gel chromatography
  7. washeluting with methylene chloride and methanol
  8. additionThe fractions containing the desired product
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b417096305a94647b233a0189c984b5b
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853258B2

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