Reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH:4]([C:12]1[N:16]2[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]2=[N:14][C:13]=1[C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)[CH2:5][CH2:6][CH:7]1OCC[O:8]1.Cl>CC(C)=O>[CH3:1][O:2][C:3](=[O:29])[CH:4]([C:12]1[N:16]2[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]2=[N:14][C:13]=1[C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)[CH2:5][CH2:6][CH:7]=[O:8]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a magnetically stirred solution of (+/−)-4-[1,3]dioxolan-2-yl-2-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-butyric acid methyl ester 35b (0.10 g, 0.253 mmol) in acetone (5 mL) at room temperature under Ar atmosphere was slowly added 5N HCl (1.5 mL). The reaction mixture was stirred for 2 h and then concentrated in vacuo to remove acetone. NaHCO3 solution (100 mL) was added until the pH is greater than 9, and the aqueous phase was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with water, dried (MgSO4), and concentrated in vacuo to provide 0.064 g (75%) of the crude product. 1H NMR (400 MHz, CDCl3) δ 2.24 (m, 4H), 2.34 (s, 3H), 2.39 (s, 3H), 3.70 (s, 3H), 4.38 (t, J=8.1 Hz, 1H), 7.03 (d, J=1.4 Hz, 1H), 7.24 (d, J=7.3 Hz, 2H), 7.56 (m, 3H), 7.99 (s, 1H), 9.48 (s, 1H).
Workup
- customat room temperature
- concentrationconcentrated in vacuo
- customto remove acetone
- additionNaHCO3 solution (100 mL) was added until the pH is greater than 9
- extractionthe aqueous phase was extracted with ethyl acetate (2×100 mL)
- washThe combined organic layers were washed with water
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-87bc952b95994704a40d551c6da0eab6
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07148353B2
Linked notes
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