Dimethylformamide → HCID 13336773, compound

HRID 1720002Notes

Reaction equation

HRID 1720002 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].[CH3:7]I.[OH2:9].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16]([OH:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1.[CH3:21][N:22]([CH3:25])[CH:23]=[O:24]>[OH-].[OH-].[Pd+2]>[C:23]([N:22]1[C:25]2[C:13](=[CH:12][CH:11]=[CH:10][CH:20]=2)[CH2:14][CH2:15][C@H:21]1[C:1]([OH:2])=[O:4])([O:9][CH2:20][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:24].[S:16]([C:13]1[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=1)([OH:19])(=[O:18])=[O:17].[NH:22]1[C:25]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:20][CH:21]1[C:1]([O:2][CH3:7])=[O:4]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 521998p-Toluenesulfonic acid monohydrate

Product 2

HCID 13336773HCID 13336773, compoundHCID 131719358HCID 131719358, compound

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

(S)-N-Carbobenzyloxy-1,2,3,4-tetra-hydroquinoline-2-carboxylic acid was prepared as described in U.S. Pat. No. 4,461,896. To a solution of this acid (18.743 g., 60.3 mmole) in dry dimethylformamide (70 ml.) at room temperature under argon was added powdered potassium carbonate (10.5 g., 76 mmole) and methyl iodide (5.6 ml., 12.8 g., 90.0 mmole). After stirring for 2 hours, the mixture was partitioned between ethyl acetate (200 ml.) and 5% potassium bisulfate (200 ml.). The organic phase was washed with water (twice) and brine, dried (sodium sulfate) and evaporated to dryness. The crude product was taken up in methanol (150 ml.), treated with p-toluenesulfonic acid, monohydrate (12.03 g., 63.2 mmole) and 20% palladium hydroxide on carbon (0.2 g.) and stirred-under an atmosphere of hydrogen (balloon) for 1.5 hours. The mixture was filtered through Celite and concentrated to a small volume, causing a crystalline solid to separate. This material was triturated with ethyl ether and the solid was collected to give a total of 19.965 g. of the titled product.

Workup

  1. customthe mixture was partitioned between ethyl acetate (200 ml.) and 5% potassium bisulfate (200 ml.)
  2. washThe organic phase was washed with water (twice) and brine
  3. dry with materialdried (sodium sulfate)
  4. customevaporated to dryness
  5. filtrationThe mixture was filtered through Celite
  6. concentrationconcentrated to a small volume
  7. customto separate
  8. customThis material was triturated with ethyl ether
  9. customthe solid was collected
  10. customto give a total of 19.965 g

Sources & evidence

ORD record
ord-43cd38856e714e60a60e9917b4646ca5
Source dataset
uspto-grants-1996_04
Patent number
US05504080

Reaction notes

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