Sodium hydride → HCID 59244623, compound

HRID 912276Notes

Reaction equation

HRID 912276 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:18][O:19][C:20](=[O:23])[CH2:21]Br>CN(C=O)C>[CH3:18][O:19][C:20](=[O:23])[CH2:21][N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:15])[C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 1516418tert-butyl N-(4-chloropyridin-2-yl)carbamate

Product 1

HCID 59244623HCID 59244623, compoundYield 289.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF suspension (1 ml) of (4-chloro-pyridin-2-yl)-carbamic acid tert-butyl ester (100 mg, 0.437 mmol), NaH (60% mineral oil dispersion, 68 mg) was added with ice cooling, followed by stirring at room temperature for 30 minutes. To the reaction mixture, bromoacetic acid methyl ester (0.19 ml, 2.06 mmol) was added, followed by stirring at room temperature for 1 hour. The reaction mixture was quenched with saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate (20 ml×2). The organic layers were combined, and washed with saturated aqueous sodium chloride solution. After the organic layer was dried over magnesium sulfate, the magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10:1), to obtain [tert-butoxycarbonyl-(4-chloro-pyridin-2-yl)-amino]-acetic acid methyl ester as a colorless liquid (380 mg, 97%).

Workup

  1. stirringby stirring at room temperature for 1 hour
  2. customThe reaction mixture was quenched with saturated aqueous ammonium chloride solution
  3. extractionfollowed by extraction with ethyl acetate (20 ml×2)
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialAfter the organic layer was dried over magnesium sulfate
  6. filtrationthe magnesium sulfate was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-2fda21711def4a579d8839855716e7f9
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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