Sodium Hydroxide → HCID 67352569, compound

HRID 446835Notes

Reaction equation

HRID 446835 reaction equation
[CH2:1]([N:8]1[CH2:32][C@:31]2([C:33](=[O:36])CO)[C@@H:10]([CH2:11][C@H:12]3[C@H:25]4[C@@:16]([F:29])([C@:17]5([CH3:28])[C:22]([C@@H:23]([F:26])[CH2:24]4)=[CH:21][C:20](=[O:27])[CH:19]=[CH:18]5)[C@@H:15]([OH:30])[CH2:14][C@@:13]32[CH3:37])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:38].[Na+]>C1COCC1.O>[CH2:1]([N:8]1[CH2:32][C@:31]2([C:33]([OH:36])=[O:38])[C@@H:10]([CH2:11][C@H:12]3[CH:25]4[C@@:16]([F:29])([C@:17]5([CH3:28])[C:22]([C@@H:23]([F:26])[CH2:24]4)=[CH:21][C:20](=[O:27])[CH:19]=[CH:18]5)[C@@H:15]([OH:30])[CH2:14][C@@:13]32[CH3:37])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53328064HCID 53328064, compound

Product 1

HCID 67352569HCID 67352569, compoundYield 33.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of compound 8 (460 mg, 0.899 mmol) and NaOH 6N (1350 μl, 11.10 mmol) in THF (20 ml) and water (10 ml) is stirred at RT for 3 days. Water is added and the organic solvent is evaporated. The basic aqueous solution (pH 12) is washed with AcOEt. The aqueous phase is then treated with HCl 6N until pH 6 when a solid precipitated. The solid is recovered by filtration and the aqueous phase is extracted with AcOEt, washed with brine, dried over Na2SO4 and then evaporated. The two fractions of obtained solid are combined and triturated with AcOEt (containing 2% MeOH) to give the title compound (150 mg, 0.301 mmol, 33.5% yield).

Workup

  1. customthe organic solvent is evaporated
  2. washThe basic aqueous solution (pH 12) is washed with AcOEt
  3. additionThe aqueous phase is then treated with HCl 6N until pH 6 when a solid
  4. customprecipitated
  5. filtrationThe solid is recovered by filtration
  6. extractionthe aqueous phase is extracted with AcOEt
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. customevaporated
  10. customtriturated with AcOEt (containing 2% MeOH)

Sources & evidence

ORD record
ord-8715e6cc525648828537aa04808b1f6f
Source dataset
uspto-grants-2013_07
Patent number
US08481517B2

Reaction notes

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