Potassium Carbonate → tert-Butyl (4-cyanobenzyl)glycinate

HRID 923567Notes

Reaction equation

HRID 923567 reaction equation
[Cl-].[C:2]([O:6][C:7](=[O:10])[CH2:8][NH3+:9])([CH3:5])([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1>CN(C=O)C.O>[C:23]([C:22]1[CH:25]=[CH:26][C:19]([CH2:18][NH:9][CH2:8][C:7]([O:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:10])=[CH:20][CH:21]=1)#[N:24]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 11095016[2-[(2-Methylpropan-2-yl)oxy]-2-oxoethyl]azanium chloride

Product 1

HCID 18000198tert-Butyl (4-cyanobenzyl)glycinateYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(tert-butoxy)-2-oxoethanaminium chloride (3.00 g, 17.9 mmol) and potassium carbonate (4.95 g, 35.8 mmol) in DMF (20 mL) was stirred at room temperature for 2 min. To the reaction mixture was added 4-(bromomethyl)benzonitrile (3.19 g, 16.3 mmol) and stirring continued for 12 h. The reaction mixture was diluted with water (50 mL) and extracted with EA (3×20 mL). The combined organic extract was dried over MgSO4 then concentrated. Purification of the crude product by a silica gel column (DCM/MeOH) gave 2.77 g (68%) of tert-butyl 2-((4-cyanobenzyl)amino)acetate INT-31 as a yellow oil. LCMS-ESI (m/z) calculated for C14H18N2O2: 246; found 247 [M+H]+, tR=0.92 min (Method 3).

Workup

  1. extractionextracted with EA (3×20 mL)
  2. extractionThe combined organic extract
  3. dry with materialwas dried over MgSO4
  4. concentrationthen concentrated
  5. customPurification of the crude product by a silica gel column (DCM/MeOH)

Sources & evidence

ORD record
ord-ea4ae8c4ccc0429898beb5e26d7d1b45
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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