Sodium Hydroxide → Ethoxy[4-(2-hydroxy-4-methylphenyl)-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]acetic acid

HRID 2406386Notes

Reaction equation

C([O:3][C:4](=[O:31])[CH:5]([O:28][CH2:29][CH3:30])[C:6]1[C:7]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:21]=2[OH:27])=[C:8]2[C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=3[S:13][C:9]2=[N:10][C:11]=1[CH3:12])C.[OH-].[Na+]>C(O)C.O1CCCC1>[CH2:29]([O:28][CH:5]([C:6]1[C:7]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:21]=2[OH:27])=[C:8]2[C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=3[S:13][C:9]2=[N:10][C:11]=1[CH3:12])[C:4]([OH:31])=[O:3])[CH3:30]

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of Ethoxy-[4-(2-hydroxy-4-methyl-phenyl)-2-methyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-3-yl]-acetic acid ethyl ester (20 mg, 45 μmols) in ethanol (1 mL) and tetrahydrofuran (1 mL) was added the sodium hydroxide (2N aqueous, 0.5 mL, 20 eq) and the reaction was stirred at 60° C. for 5 hours. The reaction was concentrated in vacuo until all organic solvents had been removed, the aqueous residue was then acidified with hydrochloric acid (2N aqueous) to pH 2. A pale yellow solid, 4 mg (16% yield) was filtered off and analysed and found to contain ethoxy-[4-(2-hydroxy-4-methyl-phenyl)-2-methyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-3-yl]-acetic acid. LC-MS (12 min acidic) 5.04 mins 47-43% pure by UV, ES+/APCI+ 412, ES−/APCI− 410; 5.80 mins 12-13% pure by UV, ES+/APCI+ 412, ES−/APCI− 410.

Workup

concentrationThe reaction was concentrated in vacuo until all organic solvents
customhad been removed
filtrationA pale yellow solid, 4 mg (16% yield) was filtered off
customLC-MS (12 min acidic) 5.04 mins 47-43%
custom5.80 mins 12-13%

Sources & evidence

ORD record: ord-c141c837836544809137109b4397bea8
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809363B2

Reaction notes

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