Hydrochloric Acid → HCID 66603412, compound

HRID 1627861Notes

Reaction equation

HRID 1627861 reaction equation
C[C:2]([C:9]1[C:10]([C:22]([CH3:25])([CH3:24])[CH3:23])=[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>C(O)C>[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]([CH3:25])([CH3:24])[CH3:23])[C:9]=1[CH:2]([CH2:6][CH2:7][CH3:8])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86662961HCID 86662961, compound

Product 1

HCID 66603412HCID 66603412, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of Methyl[2-methyl-4-(tert-butyl)-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3-yl]pentanoate (0.035 g, 0.097 mmol) in ethanol (1.0 mL) was added a solution of sodium hydroxide 10 N (0.10 ml) and the mixture was heated in a sealed tube at 100° 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 magnesium sulphate, filtered and concentrated under reduced pressure. The residue was crystallized from ethyl acetate to afford 0.015 g (44%) 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 magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-041d8ea01a20499eacd781a31b617c2f
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

Loading…