Methanol → HCID 89824944, compound

HRID 2277092Notes

Reaction equation

HRID 2277092 reaction equation
[Li+].[OH-].C[O:4][C:5]([C@@H:7]1[CH2:12][N:11]([CH3:13])[CH2:10][CH2:9][N:8]1[C:14](=[O:24])[C@H:15]([O:20]C(=O)C)[C:16]([CH3:19])([CH3:18])[CH3:17])=[O:6].C1COCC1.CO>O>[OH:20][C@H:15]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:14]([N:8]1[CH2:9][CH2:10][N:11]([CH3:13])[CH2:12][C@H:7]1[C:5]([OH:6])=[O:4])=[O:24]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 89835589HCID 89835589, compound

Product 1

HCID 89824944HCID 89824944, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of LiOH (0.016 g, 0.66 mmol) in water (2 mL) was added to a stirred solution of (S)-methyl-1-{(R)-2-acetoxy-3,3-dimethylbutanoyl}-4-methylpiperazine-2-carboxylate (0.07 g, 0.22 mmol) in a 1:1 THF:MeOH mixture (3 mL) and the reaction mixture was stirred at room temperature for 2 h. The solvent was removed under reduced pressure and the residue was dissolved in water (10 mL), acidified with 1M aqueous HCl to pH 2-3 and extracted with EtOAc (2×20 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to afford the title compound (0.034 g) as a colorless oil.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in water (10 mL)
  3. extractionextracted with EtOAc (2×20 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-906d842ff5684e1e8e20470856bd13d3
Source dataset
uspto-grants-2015_09
Patent number
US09133147B2

Reaction notes

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