Hydrochloric Acid → HCID 66597206, compound

HRID 1627856Notes

Reaction equation

HRID 1627856 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]([CH2:26][O:27][CH3:28])[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]([CH2:26][O:27][CH3:28])[C:22]([OH:24])=[O:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66597450HCID 66597450, compound

Product 1

HCID 66597206HCID 66597206, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 2-[2-Methyl-4-(4-methylphenyl)-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3-yl]-3-methoxypropanoate (0.124 g; 0.31 mmol) in methanol (3.1 mL) was added a solution of sodium hydroxide 10 N (0.31 ml) and the mixture was heated to 50° C. for 18 h. After cooling, the reaction mixture was carefully 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 0.038 g (32%) of the title compound as a beige powder.

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-b7f6af9557bc495bad6c0fbfbb341576
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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