Ethylamine → tert-Butyl N-ethylglycinate

HRID 1954680Notes

Reaction equation

HRID 1954680 reaction equation
[CH2:1]([NH2:3])[CH3:2].C(N(CC)CC)C.Br[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>C(O)C>[NH:3]([CH2:1][CH3:2])[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 8471TriethylamineHCID 79177tert-Butyl bromoacetate

Product 1

HCID 15481671tert-Butyl N-ethylglycinateYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirring solution of ethylamine (24 mL, 300 mmol) and triethylamine (14 mL, 100 mmol) in ethanol (200 mL) at 0° C., was added via addition funnel a solution of t-butyl bromoacetate (19.5 mL, 100 mmol) in ethanol (50 mL). The cold bath was left unattended and the mixture was allowed to slowly warm to room temperature. After 24 hours, the solvents were removed in vacuo. The residue was dissolved in ethyl acetate, and extracted twice with 1N citric acid. The combined aqueous layers were basified to pH 10 with solid Na2CO3, and then extracted twice with ethyl acetate. The combined ethyl acetate extracts were dried (MgSO4), filtered, and concentrated in vacuo to give 9.8 g (62%) of a yellow oil.

Workup

  1. waitThe cold bath was left
  2. customthe solvents were removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. extractionextracted twice with 1N citric acid
  5. extractionextracted twice with ethyl acetate
  6. dry with materialThe combined ethyl acetate extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-90ca9fce3c86483bb0690a509f506342
Source dataset
uspto-grants-2000_09
Patent number
US06124277

Reaction notes

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