Potassium Hydroxide → 2-{[1-Methyl-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoic acid

HRID 1359229Notes

Reaction equation

HRID 1359229 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=4[C:16]=3[C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:27][CH:28]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]([O:31]CC)=[O:30].[OH-].[K+]>C1COCC1.O>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=4[C:16]=3[C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:27][CH:28]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]([OH:31])=[O:30]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 12082839Ethyl 2-{[1-methyl-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate

Product 1

HCID 103009422-{[1-Methyl-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure described in Step 4 of Example 6, ethyl 2-{[1-methyl-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate (0.495 g, 0.926 mmol) was hydrolyzed with potassium hydroxide (0.153 g, 2.73 mmol) in THF (7.5 mL) and water (7.5 mL) to afford 2-{[1-methyl-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoic acid. Conversion to the sodium salt by treating with 1N sodium hydroxide (0.72 mL, 0.72 mmol) in methanol (12 mL) furnished the title compound as a cream-colored solid (0.228 g), mp 221-222° C. Mass spectrum (+ESI, [M+H]+) m/z 507. 1HNMR (500 MHz, DMSO-d6): δ8.25 (d, 1H, J=1.7 Hz), 8.0-8.05 (m, 2H), 7.75-7.8 (m, 2H), 7.7 (dd, 1H, J=7.3 Hz and 0.8 Hz), 7.35-7.45 (m, 4H), 7.15 (t, 1H, J=7.3 Hz), 4.45 (dd, 1H, J=9.8 Hz and 3.1 Hz), 3.25 (dd, 1H, J=13.9 Hz and 2.7 Hz), 3.05 (q, 1H, J=7.9 Hz), 2.7 (t, 2H, J=7.3 Hz), 2.4 (s, 3H), 1.5-1.55 (m, 2H), 1.1-1.15 (m, 2H), and 0.7 ppm (t, 3H, J=7.4 Hz). Elemental Analysis for C33H30O5Na: Calculated: C, 74.99; H, 5.53; N, 0.00. Found: C, 74.63; H, 5.38; N, 0.08.

Sources & evidence

ORD record
ord-86e499c532e248d98d87eb5e0622f9d6
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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