Triethylamine → Methyl 3-((2-(tert-butoxy)-2-oxoethyl)amino)propanoate

HRID 841137Notes

Reaction equation

HRID 841137 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11](=[O:15])[CH2:12][CH2:13][NH2:14].Br[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>C(Cl)Cl>[CH3:9][O:10][C:11](=[O:15])[CH2:12][CH2:13][NH:14][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79177tert-Butyl bromoacetateHCID 2734767Methyl 3-aminopropanoate hydrochloride

Product 1

HCID 14845245Methyl 3-((2-(tert-butoxy)-2-oxoethyl)amino)propanoateYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Triethylamine (7 mL, 50 mmol) was added to a solution of β-alanine methyl ester hydrochloride (5.25 g, 37.5 mmol) in methylene chloride (100 mL). The solution was cooled to 0° C. and t-butyl bromoacetate (4.88 g, 25 mmol) in methylene chloride (100 mL) was then added. The reaction mixture was warmed to room temperature and stirred overnight. The solvent was removed in vacuo and the residue was taken up in ethyl acetate. The ethyl acetate was washed with saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated in vacuo; 0.80 g (14% yield).

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. customThe solvent was removed in vacuo
  3. washThe ethyl acetate was washed with saturated NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e51e580066c04d04b3613901de4d82bf
Source dataset
uspto-grants-2002_04
Patent number
US06369034B1

Reaction notes

Loading…