Sodium Hydroxide → Pemafibrate

HRID 1712175Notes

Reaction equation

HRID 1712175 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:41]=[CH:42][CH:43]=1)[O:27][C@H:28]([CH2:39][CH3:40])[C:29]([O:31]CC1C=CC=CC=1)=[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:41]=[CH:42][CH:43]=1)[O:27][C@H:28]([CH2:39][CH3:40])[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 11856279benzyl (R)-2-[3-[N-(benzoxazol-2-yl)-N-(3-(4-methoxyphenoxy)propyl)aminomethyl]phenoxy]butyrate

Product 1

HCID 11526038PemafibrateYield 100.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Benzyl (R)-2-[3-[N-(benzoxazol-2-yl)-N-(3-(4-methoxyphenoxy)propyl)aminomethyl]phenoxy]butyrate (72 mg) was dissolved in ethanol (3 mL), and a 4 N aqueous sodium hydroxide solution (0.5 mL) was added at 0° C. Then, the resulting mixture was stirred at room temperature for 1 hour. The reaction liquor was concentrated under reduced pressure, and then was dissolved in chloroform (30 mL). The solution was washed with a saturated aqueous solution of ammonium chloride and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by preparative TLC (chloroform/methanol=10/1) to obtain a colorless solid (61 mg, 100%).

Workup

  1. concentrationThe reaction liquor was concentrated under reduced pressure
  2. dissolutionwas dissolved in chloroform (30 mL)
  3. washThe solution was washed with a saturated aqueous solution of ammonium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by preparative TLC (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-37f4e4f616f5467692da97ccb024f245
Source dataset
uspto-grants-2010_09
Patent number
US07790903B2

Reaction notes

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