Potassium Carbonate → (S)-2-Hydroxy-4-methoxy-N-(5-methylpyridin-2-yl)butanamide

HRID 1098119Notes

Reaction equation

HRID 1098119 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][C@@H:11]([CH2:22][CH2:23][O:24][CH3:25])[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][N:16]=1)=[O:13])(=O)C.OS([O-])(=O)=O.[K+]>CO>[OH:10][C@@H:11]([CH2:22][CH2:23][O:24][CH3:25])[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][N:16]=1)=[O:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 516920Potassium bisulfateHCID 57504605(S)-4-methoxy-1-(5-methylpyridin-2-ylamino)-1-oxobutan-2-yl acetate2×

Product 1

HCID 57504483(S)-2-Hydroxy-4-methoxy-N-(5-methylpyridin-2-yl)butanamideYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous potassium carbonate 1M (5.257 mL, 5.26 mmol) was added to a solution of (S)-4-methoxy-1-(5-methylpyridin-2-ylamino)-1-oxobutan-2-yl acetate (Intermediate F2) (170 mg, 0.64 mmol) in MeOH (0.3 mL) at 0° C. and the mixture was stirred at room temperature for 2 h. The reaction mixture was neutralized with aqueous KHSO4 (1.0 M, 0.29 mL). The reaction mixture was concentrated and the residue was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane to afford (S)-2-hydroxy-4-methoxy-N-(5-methylpyridin-2-yl)butanamide (142 mg, 99%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane

Sources & evidence

ORD record
ord-18f7ec8c3c46402aa3ec7e0ae9f2a0fa
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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