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

HRID 2235914

Reaction equation

HRID 2235914 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-bf5ad7e4c04748eab4d1b060eecba414
Source dataset
uspto-grants-2010_05
Patent number
US07714004B2

Linked notes

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