Potassium Carbonate → HCID 86592024, compound

HRID 1785892Notes

Reaction equation

HRID 1785892 reaction equation
C([O:3][C:4](=[O:40])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C@H:20]([N:27]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)[C:28](=[O:31])[CH2:29][CH3:30])[CH2:19][C@@H:18]2[CH3:39])=[O:16])=[CH:11][CH:10]=1)C.C(=O)([O-])[O-].[K+].[K+]>O.CO>[Cl:38][C:35]1[CH:34]=[CH:33][C:32]([N:27]([C:28](=[O:31])[CH2:29][CH3:30])[C@H:20]2[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:17]([C:15]([C:12]3[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:40])=[O:3])=[CH:14][CH:13]=3)=[O:16])[C@@H:18]([CH3:39])[CH2:19]2)=[CH:37][CH:36]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86592022HCID 86592022, compound2×

Product 1

HCID 86592024HCID 86592024, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(±)-Cis-4-(4-{4-[(4-chloro-phenyl)-propionyl-amino]-2-methyl-3,4-dihydro-2H-quinoline1-carbonyl}-phenoxy)-butyric acid was prepared from (±)-cis-4-(4-{4-[(4-chloro-phenyl)-propionyl-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-butyric acid ethyl ester. Potassium carbonate (300 mg) was dissolved in water (5 mL) and (±)-cis-4-(4-{4-[(4-chloro-phenyl)-propionyl-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-butyric acid ethyl ester (171 mg, 0.303 mmol) was dissolved in methanol (5 mL) was added. The reaction was allowed to stir over night at room temperature. The methanol was removed in vacuo and hydrochloric acid (1 N) was added until acidic. Dichloromethane was added, extracted 2×; the combined organics were dried over magnesium sulfate, filtered and concentrated to afford the carboxylic acid (50 mg, 31%).

Workup

  1. additionwas added
  2. customThe methanol was removed in vacuo and hydrochloric acid (1 N)
  3. additionwas added until acidic
  4. additionDichloromethane was added
  5. extractionextracted 2×
  6. dry with materialthe combined organics were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-71b3d92592b640719bd69b02e377bc0e
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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