Sodium Hydroxide → Pemafibrate

HRID 1712177Notes

Reaction equation

HRID 1712177 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:23][C:24]1[CH:25]=[C:26]([CH:38]=[CH:39][CH:40]=1)[O:27][C@H:28]([CH2:36][CH3:37])[C:29]([O:31]CCCC)=[O:30])[CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.[OH-].[Na+]>C(O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:23][C:24]1[CH:25]=[C:26]([CH:38]=[CH:39][CH:40]=1)[O:27][C@H:28]([CH2:36][CH3:37])[C:29]([OH:31])=[O:30])[CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11856280Butyl (2R)-2-[3-[[2-benzoxazolyl[3-(4-methoxyphenoxy)propyl]amino]methyl]phenoxy]butanoate

Product 1

HCID 11526038PemafibrateYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

n-Butyl (R)-2-[3-[N-(benzoxazol-2-yl)-N-(3-(4-methoxyphenoxy)propyl)aminomethyl]phenoxyl]butyrate (68 mg) was dissolved in ethanol (2 mL), and a 4 N aqueous sodium hydroxide solution (0.2 mL) was added at 0° C. Then, the resulting mixture was stirred at room temperature for 3 hours. Ethanol was distilled off, and water was added, and then the reaction liquor was acidified with concentrated hydrochloric acid in an ice-cold bath. The reaction liquor was extracted with ethyl acetate, and the extract was washed with water and saturated brine, and dried over dry sodium sulfate. The solution was filtered and concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (chloroform/methanol=10/1) to obtain a colorless solid (60 mg, 100%).

Workup

  1. distillationEthanol was distilled off
  2. additionwater was added
  3. customthe reaction liquor was acidified with concentrated hydrochloric acid in an ice-cold bath
  4. extractionThe reaction liquor was extracted with ethyl acetate
  5. washthe extract was washed with water and saturated brine
  6. dry with materialdried over dry sodium sulfate
  7. filtrationThe solution was filtered
  8. concentrationconcentrated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-55651e2e4cf2444eab2a1dfcbbe16a83
Source dataset
uspto-grants-2010_09
Patent number
US07790903B2

Reaction notes

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