Methanol → 2-[5-(3-{[5-(4-ethyl-1,3-thiazol-2-yl)-2-pyridinyl]oxy}propoxy)-1H-indol-1-yl]propanoic acid

HRID 2424975노트

반응식

HRID 2424975 반응식
[OH-].[Li+].[CH2:3]([C:5]1[N:6]=[C:7]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[N:26]([CH:30]([CH3:35])[C:31]([O:33]C)=[O:32])[CH:25]=[CH:24]4)=[N:14][CH:15]=2)[S:8][CH:9]=1)[CH3:4].CO.O>C1COCC1>[CH2:3]([C:5]1[N:6]=[C:7]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[N:26]([CH:30]([CH3:35])[C:31]([OH:33])=[O:32])[CH:25]=[CH:24]4)=[N:14][CH:15]=2)[S:8][CH:9]=1)[CH3:4]

참가 물질

6

반응물 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 57845392methyl 2-[5-(3-{[5-(4-ethyl-1,3-thiazol-2-yl)-2-pyridinyl]oxy}propoxy)-1H-indol-1-yl]propanoate

생성물 1

HCID 115397032-[5-(3-{[5-(4-ethyl-1,3-thiazol-2-yl)-2-pyridinyl]oxy}propoxy)-1H-indol-1-yl]propanoic acid수율 83.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Lithium hydroxide (0.05 g, 2.15 mmol) was added to a solution of methyl 2-[5-(3-{[5-(4-ethyl-1,3-thiazol-2-yl)-2-pyridinyl]oxy}propoxy)-1H-indol-1-yl]propanoate (Example 69, 0.1 g, 0.21 mmol) in a mixture of THF (2 mL), methanol (2 mL), and water (1 mL). The reaction mixture was stirred at rt for 18 h and then concentrated under reduced pressure. The residue was diluted with water and acidified with 5% H3PO4. The aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried over Na2SO4, filtered, and concentrated to give the title compound as a solid (0.079 g, 82%). 1H NMR (400 MHz, CD2Cl2) δ 8.45 (dd, 1H), 7.94 (dd, 1H), 7.08-6.62 (m, 6H), 6.22 (d, 1H), 4.94 (qt, 1H), 4.37 (t, 2H), 4.00 (t, 2H), 2.66 (qt, 2H), 2.31-2.07 (m, 2H), 1.60 (d, 3H), 1.15 (t, 3H).

후처리

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-dcfa237f98834a3ea9e5130d4176b7ff
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07964622B2

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