Methanol → ((1S)-5-{2-[6-(4-methoxyphenyl)-3-methyl-2-pyridinyl]ethoxy}-2,3-dihydro-1H-inden-1-yl)acetic acid

HRID 2235975Notes

Reaction equation

HRID 2235975 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][C@H:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][CH2:17][C:18]3[C:23]([CH3:24])=[CH:22][CH:21]=[C:20]([C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=4)[N:19]=3)=[CH:12][CH:13]=2)[CH2:8][CH2:7]1)C.[Li+].[OH-].CO.O>C1COCC1>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([C:20]2[N:19]=[C:18]([CH2:17][CH2:16][O:15][C:11]3[CH:10]=[C:9]4[C:14](=[CH:13][CH:12]=3)[C@H:6]([CH2:5][C:4]([OH:33])=[O:3])[CH2:7][CH2:8]4)[C:23]([CH3:24])=[CH:22][CH:21]=2)=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 59300434ethyl((1S)-5-{2-[6-(4-methoxyphenyl)-3-methyl-2-pyridinyl]ethoxy}-2,3-dihydro-1H-inden-1-yl)acetate

Product 1

HCID 59300443((1S)-5-{2-[6-(4-methoxyphenyl)-3-methyl-2-pyridinyl]ethoxy}-2,3-dihydro-1H-inden-1-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure described above (Example 472, step 2) and starting with ethyl((1S)-5-{2-[6-(4-methoxyphenyl)-3-methyl-2-pyridinyl]ethoxy}-2,3-dihydro-1H-inden-1-yl)acetate (Example 481, 90 mg, 0.190 mmol) and LiOH (50 mg, 1.91 mmol) in a mixture of THF (4 mL), MeOH (5 mL), and water (2 mL), the title compound was obtained (0.052 g, 65%). 1H NMR (400 MHz, CD2Cl2) δ 7.96 (d, 2H), 7.52-7.45 (m, 2H), 7.09 (d, 1H), 6.96 (d, 2H), 6.83 (d, 1H), 6.74 (dd, 1H), 4.49 (t, 2H), 3.86 (s, 3H), 3.50 (qt, 1H), 3.31 (t, 2H), 2.96-2.75 (m, 3H), 2.52-2.35 (m, 5H), 1.82-1.73 (m, 1H); LC-MS: RT=2.48 min, (M+H)+ 418.2.

Sources & evidence

ORD record
ord-adba9398a852464d80b7007942bf74df
Source dataset
uspto-grants-2010_05
Patent number
US07714004B2

Reaction notes

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