Sodium Hydroxide → HCID 9916018, compound

HRID 2056638Notes

Reaction equation

HRID 2056638 reaction equation
C([O:3][C:4](=[O:41])[CH:5]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([N:30]([C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:31][CH:32]([CH3:34])[CH3:33])[CH:25]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:23])[C:15]2[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:22])=[CH:9][CH:8]=1)C.[OH-].[Na+]>CO.O1CCCC1>[Cl:21][C:20]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:22])[C:15]=1[C:14]([NH:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH:5]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N:30]([C:35](=[O:40])[C:36]([CH3:39])([CH3:37])[CH3:38])[CH2:31][CH:32]([CH3:34])[CH3:33])[CH:25]=2)[C:4]([OH:41])=[O:3])=[CH:8][CH:9]=1)=[O:23]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69308922HCID 69308922, compound

Product 1

HCID 9916018HCID 9916018, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Thus obtained 3-[4-(2,6-dichlorobenzoyl amino) phenyl]-2-{3-[(2,2-dimethylpropionyl)isobutylamino]phenyl}propionic acid ethyl ester (1.7 g, 2.8 mmol) was dissolved in a mixed solvent of methanol (15 mL) and tetrahydrofuran (15 mL), and added with a 2 mol/L aqueous sodium hydroxide solution (15 mL, 30 mmol). The solvent was evaporated under reduced pressure, and the resultant residue was added with water to solubilize, and washed with diethyl ether. The separated aqueous phase was added with a 1 mol/L hydrochloric acid solution so as to adjust pH of the solution to as low as below 4. The solution was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and evaporated under reduced pressure so as to remove the solvent, to thereby obtain 3-[4-(2,6-dichlorobenzoylamino)phenyl]-2-{3-[(2,2-dimethylpropionyl)isobutylamino]phenyl}propionic acid (yield: 1.6 g, yield ratio: 99%) as a light-yellow solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe resultant residue was added with water
  3. washwashed with diethyl ether
  4. additionThe separated aqueous phase was added with a 1 mol/L hydrochloric acid solution so as
  5. extractionThe solution was extracted with ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure so as
  8. customto remove the solvent

Sources & evidence

ORD record
ord-163eb81e60714576983cf278904fbc45
Source dataset
uspto-grants-2008_02
Patent number
US07335673B2

Reaction notes

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