Potassium Carbonate → HCID 57595521, compound

HRID 1786044Notes

Reaction equation

HRID 1786044 reaction equation
[C:1]([N:4]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([C:17]2[S:21][C:20]([C:22]([O:24]C)=[O:23])=[CH:19][CH:18]=2)=[O:16])[C@@H:7]([CH3:26])[CH2:6]1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO.O>[C:1]([N:4]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([C:17]2[S:21][C:20]([C:22]([OH:24])=[O:23])=[CH:19][CH:18]=2)=[O:16])[C@@H:7]([CH3:26])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 11496724HCID 11496724, compound

Product 1

HCID 57595521HCID 57595521, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 5-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}thiophene-2-carboxylate (80 mg, 0.17 mmol, 1 eq.) was dissolved in methanol (6 ml). A solution of potassium carbonate (200 mg, 1.4 mmol, 8 eq.) in water (2 ml) was added and reaction mixture was stirred at room temperature for 20 h. The mixture was concentrated and the residue was acidified with a 1N HCl aqueous solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated to give 5-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydro-quinolin-1(2H)-yl]carbonyl}thiophene-2-carboxylic acid (76 mg, 99%).

Workup

  1. customreaction mixture
  2. concentrationThe mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e068d883520640a5909f8a4952974228
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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