Triethylamine → HCID 90282143, compound

HRID 1497548Notes

Reaction equation

HRID 1497548 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:5][CH:4]=1.Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(N(CC)CC)C>C(#N)C>[C:13]([O:12][C:10](=[O:11])[CH2:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][NH:1][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:4][CH:5]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79177tert-Butyl bromoacetateHCID 18334392HCID 18334392, compound

Product 1

HCID 90282143HCID 90282143, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl [4-(aminomethyl)phenyl]acetate (1.00 g) in acetonitrile (15.0 mL) were added tert-butyl bromoacetate (0.668 mL) and triethylamine (0.693 mL), followed by stirring at room temperature for 4 hours. The reaction suspension was concentrated under reduced pressure, and then to the residue was added ethyl acetate. The organic layer was washed with 0.1 M hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl N-[4-(2-tert-butoxy-2-oxoethyl)benzyl]glycinate (747 mg).

Workup

  1. concentrationThe reaction suspension was concentrated under reduced pressure
  2. additionto the residue was added ethyl acetate
  3. washThe organic layer was washed with 0.1 M hydrochloric acid
  4. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution in this order, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-cd06aaa99ad742069de5b14cd0a9ba89
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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