Water → N-[(1,1-Dimethylethoxy)carbonyl]-N-(6-methyl-2-pyridinyl)glycine 1,1-dimethylethyl ester

HRID 2359808Notes

Reaction equation

HRID 2359808 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].O>CN(C)C=O>[C:23]([O:22][C:20](=[O:21])[CH2:19][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 11367776tert-Butyl (6-methylpyridin-2-yl)carbamate

Product 1

HCID 86651793N-[(1,1-Dimethylethoxy)carbonyl]-N-(6-methyl-2-pyridinyl)glycine 1,1-dimethylethyl esterYield 101.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(tert-butoxycarbonylamino)-6-methylpyridine (723 mg, 3.47 mmol) in N,N-dimethylformamide (11.5 ml) was added sodium hydride (mineral oil 55% dispersion) (0.18 g, 4.2 mmol) in portions under ice cooling. After stirring at room temperature for 30 minutes, tert-butyl bromoacetate (0.62 ml, 4.2 mmol) was added dropwise under ice cooling, followed by stirring at room temperature for 2 hours. After completion of the reaction, water was added to the reaction solution, followed by extraction with ethyl acetate. The separated organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=10:1→5:1 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (1.14 g) substantially quantitatively as a colorless liquid.

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. additionwas added to the reaction solution
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe separated organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additioncontaining the desired compound
  8. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-c51eee7250274980b7f9bb5bf3adbca3
Source dataset
uspto-grants-2014_04
Patent number
US08685986B2

Reaction notes

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