Hydrochloric Acid → HCID 66597220, compound

HRID 1627858Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of Methyl[2-methyl-4-(2-furyl)-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3-yl]pentanoate (0.335 g, 0.907 mmol) in methanol (9 mL) was added a solution of sodium hydroxide 10 N (0.9 ml) and the mixture was heated at 100° C. for 18 h in a sealed tube. After cooling, the reaction mixture was acidified with 1N HCl (pH˜2) and partially concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was crystallized from a mixture of ethyl acetate/heptane to afford 0.219 g (68%) of the title compound as a white solid.

Workup

temperatureAfter cooling
concentrationpartially concentrated under reduced pressure
customThe residue was partitioned between ethyl acetate and water
washThe organic layer was washed with brine
dry with materialdried over sodium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was crystallized from a mixture of ethyl acetate/heptane

Sources & evidence

ORD record: ord-6cbc5bd92e05429abce0002d88024c94
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785638B2

Reaction notes

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