Hydrochloric Acid → HCID 66597203, compound

HRID 1627854Notes

Reaction equation

HRID 1627854 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH2:13][CH2:12][CH2:11][C:10]=3[C:5]2=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:3]=1[CH:21]([CH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)[C:22]([O:24]C)=[O:23].[OH-].[Na+].Cl>CO>[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH2:13][CH2:12][CH2:11][C:10]=3[C:5]2=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:3]=1[CH:21]([CH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)[C:22]([OH:24])=[O:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66597185HCID 66597185, compound

Product 1

HCID 66597203HCID 66597203, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 2-[2-Methyl-4-p-tolyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3-yl]-2-cyclopentylacetate (0.077 g; 0.18 mmol) in methanol (1.8 mL) was added a solution of sodium hydroxide 10 N (0.18 ml) and the mixture was heated to 60° C. for 18 h. 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 0.029 g (40%) of the title compound as a white solid.

Workup

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

Sources & evidence

ORD record
ord-fc2c996549734e44a1636b2ae7c73166
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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