Potassium Carbonate → HCID 10965616, compound

HRID 923618Notes

Reaction equation

HRID 923618 reaction equation
Cl.[NH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5].Br[CH2:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[C:14]([C:13]1[CH:16]=[CH:17][C:10]([CH2:9][NH:2][CH2:3][C:4]([O:6][CH3:7])=[O:5])=[CH:11][CH:12]=1)#[N:15]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 10965616HCID 10965616, compoundYield 21.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Prepared using General Procedure 13. To a stirred solution of methyl 2-aminoacetate hydrochloride (5.07 g, 40.4 mmol) and 4-(bromomethyl)benzonitrile (7.20 g, 36.7 mmol) in DMF (40 mL) was added potassium carbonate (11.2 g, 81 mmol). After stirring at room temperature for 3 h the reaction mixture was diluted with water (300 mL) and the product extracted into EA (200 mL). The organics were washed with water (200 mL), dried over MgSO4 and concentrated in vacuo. The crude product was purified by chromatography (MeOH/DCM) to afford 1.6 g (21%) of methyl 2-((4-cyanobenzyl)amino)acetate INT-73 as a clear oil. LCMS-ESI (m/z) calculated for C11H12N2O2: 204; found 205 [M+H]+, tR=0.4 min (Method 10).

Workup

  1. customPrepared
  2. extractionthe product extracted into EA (200 mL)
  3. washThe organics were washed with water (200 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-f07b482aab2347848cc131cf0d1262aa
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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