Hydrochloric Acid → ((1S)-5-{2-[(2,6-Dimethyl-3-pyridinyl)oxy]ethoxy}-2,3-dihydro-1H-inden-1-yl)acetic acid

HRID 2235914

반응식

HRID 2235914 반응식
[CH3:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[C@H:17]([CH2:21][C:22]([O:24]CC)=[O:23])[CH2:16][CH2:15]3)=[CH:6][CH:5]=[C:4]([CH3:27])[N:3]=1.O.[Li+].[OH-].Cl>C1COCC1.CCO>[CH3:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[C@H:17]([CH2:21][C:22]([OH:24])=[O:23])[CH2:16][CH2:15]3)=[CH:6][CH:5]=[C:4]([CH3:27])[N:3]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 59300516ethyl ((1S)-5-{2-[(2,6-dimethyl-3-pyridinyl)oxy]ethoxy}-2,3-dihydro-1H-inden-1-yl)acetate

생성물 1

HCID 59300509((1S)-5-{2-[(2,6-Dimethyl-3-pyridinyl)oxy]ethoxy}-2,3-dihydro-1H-inden-1-yl)acetic acid수율 91%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ethyl ((1S)-5-{2-[(2,6-dimethyl-3-pyridinyl)oxy]ethoxy}-2,3-dihydro-1H-inden-1-yl)acetate (Example 250, 43.1 mg, 0.12 mmol) in a mixture of THF (2 mL), water (2 mL), and EtOH (1 mL), was added LiOH (11.5 mg, 0.48 mmol). The reaction mixture was vigorously stirred for 24 h, acidified to pH ˜5 with HCl (1N aqueous solution), and then extracted with CH2Cl2. The combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure to give the title compound as a white solid (36.2 mg, 91%). 1H NMR (400 MHz, CDCl3) δ 1.72-1.75 (m, 1H), 2.33-2.44 (m, 2H), 2.37 (s, 3H), 2.41 (s, 3H), 2.68-2.85 (m, 3H), 3.52-3.55 (m, 1H), 4.19-4.25 (m, 4H), 6.67 (d, 1H), 6.74 (s, 1H) 6.85 (d, 1H), 6.99 (d, 1H), 7.01 (d, 1H); LCMS: RT=2.41 min, (M+H)+ 342.3.

후처리

  1. extractionextracted with CH2Cl2
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-bf5ad7e4c04748eab4d1b060eecba414
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07714004B2

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