Sodium Hydroxide → HCID 59659328, compound

HRID 2056643Notes

Reaction equation

HRID 2056643 reaction equation
C([O:3][C:4](=[O:33])[CH:5]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([N:22]([C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:23][CH:24]([CH3:26])[CH3:25])[CH:15]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1)C.[OH-].[Na+]>CO.O1CCCC1>[Br:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][CH:5]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([N:22]([C:27](=[O:32])[C:28]([CH3:29])([CH3:31])[CH3:30])[CH2:23][CH:24]([CH3:26])[CH3:25])[CH:15]=2)[C:4]([OH:33])=[O:3])=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69308429HCID 69308429, compound

Product 1

HCID 59659328HCID 59659328, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Thus obtained 3-(4-bromophenyl)-2-{3-[(2,2-dimethylpropionyl)isobutylamino]-4-methoxyphenyl} propionic acid ethyl ester (104 mg, 0.2 mmol) was dissolved in a mixed solvent of methanol (3 mL) and tetrahydrofuran (3 mL), and the mixture was added with a 2 mol/L aqueous sodium hydroxide solution (3 mL, 6 mmol). The solution was evaporated under reduced pressure so as to remove the solvent, 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 as low as 4 or below. The solution was then extracted with ethyl acetate, the extract was dried over anhydrous sodium sulfate, evaporated under reduced pressure so as to remove the solvent, to thereby obtain 3-(4-bromophenyl)-2-{3-[(2,2-dimethylpropionyl)isobutyl amino]-4-methoxyphenyl}propionic acid (yield: 89 mg, yield ratio: 90%) as a white solid.

Workup

  1. customThe solution was evaporated under reduced pressure so as
  2. customto remove the solvent
  3. additionthe resultant residue was added with water
  4. dissolutionto be dissolved
  5. washthe solution was washed with diethyl ether
  6. additionThe separated aqueous phase was added with a 1 mol/L hydrochloric acid so as
  7. extractionThe solution was then extracted with ethyl acetate
  8. dry with materialthe extract was dried over anhydrous sodium sulfate
  9. customevaporated under reduced pressure so as
  10. customto remove the solvent

Sources & evidence

ORD record
ord-144c80a11d4f45d48e09d40632100876
Source dataset
uspto-grants-2008_02
Patent number
US07335673B2

Reaction notes

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