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

HRID 2235914

Reaktionsgleichung

Reaktionsgleichung von HRID 2235914
[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

Komponenten

7

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-bf5ad7e4c04748eab4d1b060eecba414
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07714004B2

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