Hydrochloric Acid → 3-[4-(5-Bromo-3,3-dimethyl-2-oxo-2,3-dihydroindol-1-ylmethoxy)phenyl]hex-4-ynoic acid

HRID 40484노트

반응식

HRID 40484 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:25]#[C:26][CH3:27])[CH2:20][C:21]([O:23]C)=[O:22])=[CH:15][CH:14]=1)[C:6](=[O:28])[C:5]2([CH3:30])[CH3:29].Cl.O>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:25]#[C:26][CH3:27])[CH2:20][C:21]([OH:23])=[O:22])=[CH:15][CH:14]=1)[C:6](=[O:28])[C:5]2([CH3:30])[CH3:29]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 58031723Methyl 3-[4-(5-bromo-3,3-dimethyl-2-oxo-2,3-dihydroindol-1-ylmethoxy)phenyl]-hex-4-ynoate

생성물 1

HCID 547669233-[4-(5-Bromo-3,3-dimethyl-2-oxo-2,3-dihydroindol-1-ylmethoxy)phenyl]hex-4-ynoic acid

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

실험 절차

730 mg of methyl 3-[4-(5-bromo-3,3-dimethyl-2-oxo-2,3-dihydroindol-1-ylmethoxy)phenyl]-hex-4-ynoate were dissolved in a mixture of THF/MeOH/2N NaOH=1:1:1 (5 ml of each) and stirred at room temperature. After 1 hour, the mixture was acidified to pH 1 by addition of 2N HCl. 50 ml of water were added, the mixture was extracted three times with 50 ml each time of ethyl acetate. The combined organic phases were dried over MgSO4, then concentrated under reduced pressure and purified on silica gel with the n-heptane/ethyl acetate solvent mixture as a linear gradient of 100% n-heptane=>100% ethyl acetate. This gave 620 mg of 3-[4-(5-bromo-3,3-dimethyl-2-oxo-2,3-dihydroindol-1-ylmethoxy)phenyl]-hex-4-ynoic acid.

후처리

  1. extractionthe mixture was extracted three times with 50 ml each time of ethyl acetate
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. custompurified on silica gel with the n-heptane/ethyl acetate solvent mixture as a linear gradient of 100% n-heptane=>100% ethyl acetate

출처 및 근거

ORD 기록
ord-f6ccd08ef508492a833a623e6c26aacb
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530413B2

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