Sodium Hydroxide → 5,6,7,8-Tetrahydro-2-methyl-α-(1-methylethyl)-4-(4-methylphenyl)[1]benzothieno[2,3-b]pyridine-3-acetic acid

HRID 1627882Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl [2-methyl-4-(p-tolyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]-3-methylbutanoate (0.109 g; 0.267 mmol) in methanol (2.7 mL) was added a solution of sodium hydroxide 5 N (0.53 mL) and the mixture was heated at 60° C. for 18 h. After cooling, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the mixture was acidified with HCl (1N) until pH 1. The organic layer was washed with brine, water, dried over magnesium sulphate and concentrated under reduced pressure. A purification by preparative TLC using a mixture ethyl acetate/heptane (1:1)+0.5% AcOH furnished 0.0013 g (12%) of the title compound as a light yellow solid.

Workup

temperatureAfter cooling
concentrationthe reaction mixture was concentrated under reduced pressure
dissolutionThe residue was dissolved in ethyl acetate
washThe organic layer was washed with brine, water
dry with materialdried over magnesium sulphate
concentrationconcentrated under reduced pressure
customA purification by preparative TLC

Sources & evidence

ORD record: ord-0a95352f4c39422cad56942e0c00f5d9
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785638B2

Reaction notes

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