Sodium Bicarbonate → HCID 86749070, compound

HRID 2211018Notes

Reaction equation

HRID 2211018 reaction equation
[CH2:1]([N:8]1[C@H:12]([C:13]([S:16]CC2C=CC(OC)=CC=2)([CH3:15])[CH3:14])[CH2:11][C@H:10]([CH2:26][S:27]CC2C=CC(OC)=CC=2)[C:9]1=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O.C1(SC)C=CC=CC=1.FC(F)(F)S(O)(=O)=O>[CH2:1]([N:8]1[C@H:12]([C:13]([SH:16])([CH3:15])[CH3:14])[CH2:11][C@H:10]([CH2:26][SH:27])[C:9]1=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 86749071HCID 86749071, compound

Product 1

HCID 86749070HCID 86749070, compoundYield 18.1%

Reagents, catalysts & solvents 3

HCID 6422Trifluoroacetic acidSolventHCID 7520ThioanisoleSolventHCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

To a stirred solution of cis-N-benzyl-4-[1-(4-methoxybenzylthio)-1-methylethyl]-2-(4-methoxybenzylthiomethyl )-4-butanelactam (compound No.14-1, 500 mg) in trifluoroacetic acid (4 ml), thioanisol (0.66 ml) and trifluoromethanesulfonic acid (0.50 ml) were added. After stirring for 2 hours at room temperature, the mixture was poured into a mixture of ice and saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, water and then saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was dissolved in ethanol (3 ml). To the solution sodium borohydride (20 mg) was added and the mixture was stirred for 30 minutes at room temperature. 1N hydrochloric acid was added to the mixture and extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was purified by silica gel column chromatography to give 50 mg (18%) of the titled compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe oily residue was dissolved in ethanol (3 ml)
  6. additionTo the solution sodium borohydride (20 mg) was added
  7. stirringthe mixture was stirred for 30 minutes at room temperature
  8. addition1N hydrochloric acid was added to the mixture
  9. extractionextracted with ethyl acetate
  10. washThe organic layer was washed with water and saturated sodium chloride solution
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated in vacuo
  13. customThe oily residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fdce34e02ead4dbd9ba273de02ade286
Source dataset
uspto-grants-1995_10
Patent number
US05461158

Reaction notes

Loading…