Potassium Hydroxide → HCID 22866402, compound

HRID 864468Notes

Reaction equation

HRID 864468 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:31])[C@H:7]([CH2:27][CH:28]([CH3:30])[CH3:29])[N:8]([CH3:26])[C:9](=[O:25])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:23]2[CH:22]=[CH:21][N:20]=[CH:19][C:18]=2[N:17]=[C:16]1[CH3:24])C>C(O)C>[CH3:26][N:8]([C:9](=[O:25])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:23]2[CH:22]=[CH:21][N:20]=[CH:19][C:18]=2[N:17]=[C:16]1[CH3:24])[C@H:7]([C:6]([OH:31])=[O:5])[CH2:27][CH:28]([CH3:29])[CH3:30]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22866359HCID 22866359, compound

Product 1

HCID 22866402HCID 22866402, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2M Potassium hydroxide (2.5 ml) was added to a solution of N-methyl-N-6-(2-methylimidazo[4,5-c]pyridin-1-yl)hexanoyl-L-leucine ethyl ester (200 mg, 0.50 mmol) in ethanol (70 ml). The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and water was added to the residue. The pH of the resulting solution was adjusted to pH 6 by the addition of 2M HCl, the mixture was saturated with sodium chloride and extracted with DCM. The combined organic extracts were dried over anhydrous sodium sulphate, filtered and evaporated to give N-methyl-N-6-(2-methylimidazo[4,5-c]pyridin-1-yl)hexanoyl-L-leucine (70 mg, 38%) as a white foam.

Workup

  1. customThe solvent was removed under reduced pressure and water
  2. additionwas added to the residue
  3. additionThe pH of the resulting solution was adjusted to pH 6 by the addition of 2M HCl
  4. extractionextracted with DCM
  5. dry with materialThe combined organic extracts were dried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-0919a458e87d425cb115a84f3c6c7bc2
Source dataset
uspto-grants-1996_10
Patent number
US05563151

Reaction notes

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