Hydrochloric Acid → HCID 18377368, compound

HRID 2301122Notes

Reaction equation

HRID 2301122 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15]([C:17]([OH:19])=[O:18])=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:20]CCCCC.C([Li])CCC.CI.Cl>O1CCCC1.O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15]([C:17]([OH:19])=[O:18])=[C:16]([CH3:20])[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 177503995-(tert-Butoxycarbonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylic acidHCID 178418244HCID 178418244, compound

Product 1

HCID 18377368HCID 18377368, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

5-t-Butoxycarbonyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine-2-carboxylic acid (300 mg, 1.1 mmol) was dissolved in anhydrous tetrahydrofuran (5 ml), n-butyl lithium hexane solution (15%, 1.5 ml, 2.3 mmol) was added dropwise thereto at −78° C. in an atmosphere of argon, and then the mixture was stirred for 1 hour. The reaction solution was mixed with methyl iodide (1.6 ml, 2.7 mmol) and stirred for 1 hour and then at room temperature for 1 hour. The reaction solution was mixed with ethyl acetate and hydrochloric acid (1 N) to acidify the water layer, and then the reaction product was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with anhydrous magnesium sulfate, and then the solvent was removed by evaporation under a reduced pressure and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 180 mg (0.61 mmol, 57% in yield) of the title compound.

Workup

  1. stirringstirred for 1 hour
  2. waitat room temperature for 1 hour
  3. extractionthe reaction product was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customthe solvent was removed by evaporation under a reduced pressure
  7. customthe thus obtained material was separated
  8. custompurified by a silica gel column chromatography
  9. customto obtain

Sources & evidence

ORD record
ord-a6cb165b6ea645d099a26a6fd8ca19d1
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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