Methanol → 2-Tert-butoxycarbonyl-1,2,3,4-tetrahydro-benzo[b]thieno[2,3-c]pyridine-3-carboxylic acid

HRID 893855

Reaction equation

HRID 893855 reaction equation
C(OC([C:6]1([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[S:18][C:9]23[CH:17]=[CH:16][CH:15]=[CH:14][C:10]2=[N:11][CH2:12][CH2:13][CH:8]3[CH2:7]1)=O)C.[OH-:26].[Na+].[CH3:28][OH:29]>C(Cl)(Cl)Cl>[C:22]([O:21][C:19]([CH:6]1[S:18][C:9]23[CH:17]=[CH:16][CH:15]=[CH:14][C:10]2=[N:11][CH2:12][CH2:13][CH:8]3[CH:7]1[C:28]([OH:29])=[O:26])=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 199608562-Tert-butoxycarbonyl-1,2,3,4-tetrahydrobenzo[b]thieno[2,3-c]pyridine-carboxylic acid ethyl ester

Product 1

HCID 699596062-Tert-butoxycarbonyl-1,2,3,4-tetrahydro-benzo[b]thieno[2,3-c]pyridine-3-carboxylic acidYield 75%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In a mixed solvent of 30 ml of methanol and 20 ml of chloroform was dissolved 6 g of 2-tert-butoxycarbonyl-1,2,3,4-tetrahydrobenzo[b]thieno[2,3-c]pyridine-carboxylic acid ethyl ester and 4 ml of an aqueous solution of 5N sodium hydroxide was further added thereto, and then the solution was refluxed for 5 hours. The solvents were distilled off under reduced pressure and 300 ml of 5% citric acid and 300 ml of chloroform were added to the residue. The chloroform layer was washed with a saturated aqueous sodium chloride solution and then dried by sodium sulfate. After distilling off chloroform under reduced pressure, the residue formed was recrystallized from a mixture of chloroform and hexane to provide 4.15 g (yield of 75%) of 2-tert-butoxycarbonyl-1,2,3,4-tetrahydrobenzo[b]thieno[2,3-c]pyridine-3-carboxylic acid.

Workup

  1. additionwas further added
  2. temperaturethe solution was refluxed for 5 hours
  3. distillationThe solvents were distilled off under reduced pressure and 300 ml of 5% citric acid and 300 ml of chloroform
  4. additionwere added to the residue
  5. washThe chloroform layer was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried by sodium sulfate
  7. distillationAfter distilling off chloroform under reduced pressure
  8. customthe residue formed
  9. customwas recrystallized from a mixture of chloroform and hexane

Sources & evidence

ORD record
ord-36cccc27ee4145db9b1c284e496830da
Source dataset
uspto-grants-1992_06
Patent number
US05126448

Linked notes

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