Triethylamine → HCID 178470392, compound

HRID 1492768Notes

Reaction equation

HRID 1492768 reaction equation
Cl.[NH2:2][CH:3]([C:9](=O)[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:12](=[NH:17])(OCC)[CH3:13].C(N(CC)CC)C>C(O)C>[CH3:13][C:12]1[NH:2][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:9]([CH3:10])[N:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 65066Ethyl acetimidateHCID 13282897Ethyl 2-amino-3-oxobutanoate hydrochloride

Product 1

HCID 178470392HCID 178470392, compoundYield 23.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-amino-3-oxobutanoate hydrochloride (5 g) was added portionwise to a solution of ethyl ethaneimidate (34.0 g) and triethylamine (42 ml) in ethanol (500 ml), and the resulting yellow solution was stirred overnight. Solvent was removed in vacuo and the residue partitioned between water (200 ml) and ether (200 ml). The organic layer was separated and the aqueous phase further extracted with ether (2×200 ml). The dried organic extracts were evaporated in vacuo and the residue washed with cold ether and filtered to give the title compound as a white solid (1.1 g). m.p. 165-166° C.

Workup

  1. customSolvent was removed in vacuo
  2. customthe residue partitioned between water (200 ml) and ether (200 ml)
  3. customThe organic layer was separated
  4. extractionthe aqueous phase further extracted with ether (2×200 ml)
  5. customThe dried organic extracts were evaporated in vacuo
  6. washthe residue washed with cold ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-dbf3f6160cac4904851a06223061e42a
Source dataset
uspto-grants-1994_12
Patent number
US05374646

Reaction notes

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