Sodium Hydroxide → HCID 86696595, compound

HRID 2276342Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of ethyl[2-oxo-1-propyl-4-(p-tolyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]pentanoate (0.071 g; 0.152 mmol) in a mixture of methanol and ethanol (2:1) (4.5 mL) was added a 5% sodium hydroxide solution (3.66 mL; 4.57 mmol) and the reaction mixture was heated to 90° C. for 7 h. The organic volatiles were removed under reduced pressure and the remaining basic solution was acidified to pH 2 with a 1N hydrochloric acid solution. The aqueous layer was extracted with ethyl acetate and the organics were combined, dried over sodium sulfate, concentrated under reduced pressure. Purification by preparative HPLC (method 2) furnished 0.015 g (22.7%) of 2-[2-oxo-1-propyl-4-(p-tolyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]pentanoic acid as a white solid. ESI/APCI(+): 438 (M+H).

Workup

customThe organic volatiles were removed under reduced pressure
extractionThe aqueous layer was extracted with ethyl acetate
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customPurification by preparative HPLC (method 2)

Sources & evidence

ORD record: ord-bfa4e376378d421099ccc8a123772540
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09132129B2

Reaction notes

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