Sodium Hydroxide → HCID 66597313, compound

HRID 1627857Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 2-[2-phenyl-4-p-tolyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3-yl]pentanoate (0.194 g; 0.42 mmol) in methanol (4.2 mL) was added a solution of sodium hydroxide 10 N (0.42 ml) and the mixture was heated to 60° C. for 18 h. After cooling, the reaction mixture was concentrated under reduced pressure and the crude solid was suspended in ethyl acetate and the mixture was acidified with 1N HCl (pH˜2). The organic layer was washed with brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography silica using a mixture ethyl acetate/heptane (1/1)+0.5% acetic acid as eluent to afford 0.072 g (39%) of the title compound as a white solid.

Workup

temperatureAfter cooling
concentrationthe reaction mixture was concentrated under reduced pressure
washThe organic layer was washed with brine
dry with materialdried over sodium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by preparative thin layer chromatography silica using a mixture ethyl acetate/heptane (1/1)+0.5% acetic acid as eluent

Sources & evidence

ORD record: ord-d340c981b0df47fe86495d2c25943dae
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785638B2

Reaction notes

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