Sodium Hydroxide → HCID 11570705, compound

HRID 2056642Notes

Reaction equation

HRID 2056642 reaction equation
C([O:3][C:4](=[O:43])[CH:5]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([N:32]([C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:33][CH:34]([CH3:36])[CH3:35])[CH:25]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[C:21]([Cl:22])=[CH:20][N:19]=[CH:18][C:17]=2[Cl:23])=[O:15])=[CH:9][CH:8]=1)C.[OH-].[Na+]>CO.O1CCCC1>[Cl:22][C:21]1[CH:20]=[N:19][CH:18]=[C:17]([Cl:23])[C:16]=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][C:27]([O:30][CH3:31])=[C:26]([N:32]([C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:33][CH:34]([CH3:36])[CH3:35])[CH:25]=2)[C:4]([OH:43])=[O:3])=[CH:8][CH:9]=1)=[O:15]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69308341HCID 69308341, compound

Product 1

HCID 11570705HCID 11570705, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Thus obtained 3-[4-(3,5-dichloropyridine-4-carbonylamino)phenyl]-2-{3-[(2,2-dimethylpropionyl) isobutylamino]-4-methoxyphenyl}propionic acid ethyl ester (400 mg, 0.64 mmol) was dissolved in a mixed solvent of methanol (5 mL) and tetrahydrofuran (5 mL), and added with a 2 mol/L aqueous sodium hydroxide solution (5 mL, 10 mmol). The solvent was evaporated under reduced pressure, the resultant residue was added with water to be dissolved, and the solution was washed with diethyl ether. The separated aqueous phase was added with a 1 mol/L hydrochloric acid so as to adjust pH of the solution to 5 to 7. The solution was then 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-(3,5-dichloro pyridine-4-carbonylamino)phenyl]-2-{3-[(2,2-dimethyl propionyl)isobutylamino]-4-methoxyphenyl}propionic acid (yield: 353 mg, yield ratio: 92%) as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe resultant residue was added with water
  3. dissolutionto be dissolved
  4. washthe solution was washed with diethyl ether
  5. additionThe separated aqueous phase was added with a 1 mol/L hydrochloric acid so as
  6. extractionThe solution was then extracted with ethyl acetate
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated under reduced pressure so as
  9. customto remove the solvent to thereby obtain 3-[4-(3,5-dichloro pyridine-4-carbonylamino)phenyl]-2-{3-[(2,2-dimethyl propionyl)isobutylamino]-4-methoxyphenyl}propionic acid (yield: 353 mg, yield ratio: 92%) as a white solid

Sources & evidence

ORD record
ord-383d023e6f904ca7910ed33a5e712454
Source dataset
uspto-grants-2008_02
Patent number
US07335673B2

Reaction notes

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