Triethylamine → Ethyl 3-(ethoxycarbonylmethylamino)propionate

HRID 705695Notes

Reaction equation

HRID 705695 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3].Cl.[CH2:9]([O:11][C:12](=[O:15])[CH2:13][NH2:14])[CH3:10].C(N(CC)CC)C>C(O)C>[CH2:9]([O:11][C:12](=[O:15])[CH2:13][NH:14][CH2:3][CH2:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 281012Ethyl 3-(ethoxycarbonylmethylamino)propionate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
37.5 °C

Procedure

Ethyl acrylate (11.5 g, 0.115 mol) was added to a solution of glycine ethyl ester hydrochloride (187) (20 g, 0.144 mol) and triethylamine (17.6 mL, 0.127 mol) in ethanol (134 mL) and the mixture heated to 35-40° C. for 3.5 hrs. The mixture was concentrated and partitioned between water (100 mL) and ethyl acetate (1×300 mL). The organics were washed with 1×100 mL half saturated sodium bicarbonate, 1×50 mL saturated sodium chloride, and dried over Na2SO4. The dried organics were evaporated to 20.94 g of clear colorless oil that was used in the next step without further purification. MS (ESI) m/z 204 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between water (100 mL) and ethyl acetate (1×300 mL)
  3. washThe organics were washed with 1×100 mL half saturated sodium bicarbonate, 1×50 mL saturated sodium chloride
  4. dry with materialdried over Na2SO4
  5. customThe dried organics were evaporated to 20.94 g of clear colorless oil that
  6. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-c5c5a9f5e4e747d1af4396d651719761
Source dataset
uspto-grants-2015_11
Patent number
US09174972B2

Reaction notes

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