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Acetic Acid → 3-[3-(3,3-Dimethyl-1-oxo-1-butyl)-5-(quinolin-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoic acid

HRID 1590737
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HRID 1590737 반응식
[CH3:1][C:2]([CH3:36])([CH3:35])[CH2:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16][C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=3)[CH:13]=2)[NH:8][C:7]=1[CH2:27][C:28]([CH3:34])([CH3:33])[C:29]([O:31]C)=[O:30])=[O:5].[OH-].[Na+].CC(O)=O.C(O)(C)C>CO.C1COCC1.O>[CH3:1][C:2]([CH3:36])([CH3:35])[CH2:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16][C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=3)[CH:13]=2)[NH:8][C:7]=1[CH2:27][C:28]([CH3:34])([CH3:33])[C:29]([OH:31])=[O:30])=[O:5]
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참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 18947551Methyl 3-[3-(3,3-dimethyl-1-oxo-1-butyl)-5-(quinolin-2-ylmethoxy)indol-2-yl]-2,2-dimethyl-propanoate

생성물 1

HCID 197343483-[3-(3,3-Dimethyl-1-oxo-1-butyl)-5-(quinolin-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoic acid

시약·촉매·용매 3

HCID 887
Methanol
용매
HCID 962Water용매2회
HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

The crude ester from step D was dissolved in a mixture of MeOH (20 mL), THF (20 mL), and H2O (5 mL). To this was added 10M NaOH (2.3 mL, 23 mmol). After stirring for 3 hours, the solution was cooled to 0° C., and HOAc (1.5 mL) was added dropwise. The solution was partly concentrated to remove the THF and MeOH, and the product was then extracted into EtOAc. The organic layer was washed with H2O and brine. After drying (MgSO4), the solution was filtered and evaporated to give a pale orange solid. The product was stirred vigourously with a mixture of isopropanol (30 ml) and H2O (3 mL) to give the title compound as an off-white amourphous solid (2.6 g). mp=193°-196° C. (dec)

후처리

  1. concentrationThe solution was partly concentrated
  2. customto remove the THF and MeOH
  3. extractionthe product was then extracted into EtOAc
  4. washThe organic layer was washed with H2O and brine
  5. dry with materialAfter drying (MgSO4)
  6. filtrationthe solution was filtered
  7. customevaporated
  8. customto give a pale orange solid

출처 및 근거

ORD 기록
ord-72e4ef91ff8245759f12ec34c536d1f0
출처 데이터셋
uspto-grants-1993_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05204344

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