Potassium Carbonate → HCID 86592041, compound

HRID 1785904Notes

Reaction equation

HRID 1785904 reaction equation
C[O:2][C:3](=[O:38])[CH:4]=[CH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]([C:16](=[O:24])[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[C@@H:11]([CH3:25])[CH2:10][C@H:9]2[N:26]([C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)[C:27](=[O:30])[CH2:28][CH3:29].C([O-])([O-])=O.[K+].[K+]>CO.O>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([N:26]([C:27](=[O:30])[CH2:28][CH3:29])[C@H:9]2[C:8]3[C:13](=[CH:14][CH:15]=[C:6]([CH:5]=[CH:4][C:3]([OH:38])=[O:2])[CH:7]=3)[N:12]([C:16](=[O:24])[C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[C@@H:11]([CH3:25])[CH2:10]2)=[CH:32][CH:33]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86592040HCID 86592040, compound

Product 1

HCID 86592041HCID 86592041, compoundYield 9.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of (±)-cis-3-[4-[(4-chloro-phenyl)-propionyl-amino]-1-(4-fluoro-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-6-yl]-acrylic acid methyl ester (110 mg, 0.21 mmol) in 4 ml methanol was added 50 mg K2CO3, (0.36 mmol, in 2 ml water). The resulting reaction mixture was stirred at room temperature overnight. The methanol was removed under vacuum. 1M HCl was added until the mixture was acidic. Dichloromethane (25 ml) was added. Organic layer was dried with magnesium sulfate. Dichloromethane was removed under vacuum. The residue was purified by HPLC to give 10 mg title compound.

Workup

  1. customThe resulting reaction mixture
  2. customThe methanol was removed under vacuum
  3. addition1M HCl was added until the mixture
  4. additionDichloromethane (25 ml) was added
  5. dry with materialOrganic layer was dried with magnesium sulfate
  6. customDichloromethane was removed under vacuum
  7. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-f314d735920a44cca0e0786ce89d3265
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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