Triethylamine → HCID 54208818, compound

HRID 2416683Notes

Reaction equation

HRID 2416683 reaction equation
[C:1]([CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=1[CH2:20][NH2:21])[CH2:6][C:7]([O:9][CH3:10])=[O:8])(OC)=[O:2].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]2[CH2:11][CH:5]([CH2:6][C:7]([O:9][CH3:10])=[O:8])[C:1](=[O:2])[NH:21][CH2:20][C:13]=2[CH:14]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 54445606HCID 54445606, compound

Product 1

HCID 54208818HCID 54208818, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl (±)-3-carbomethoxy-4-[2-(aminomethyl)-4-methoxyphenyl]butanoate (10 g, 24 mmol) and triethylamine (17 mL, 120 mmol) in toluene (100 mL) was heated at reflux for 18 hr. The reaction was then concentrated and the residue was partitioned between ethyl acetate and water. The aqueous layer was extracted twice with ethyl acetate and the combined organic extracts were washed with brine, dried (MgSO4), and concentrated to afford the title compound (4.8 g, 76%) as tan solid: MS (ES) m/e 264.2 (M+H)+.

Workup

  1. temperatureat reflux for 18 hr
  2. concentrationThe reaction was then concentrated
  3. customthe residue was partitioned between ethyl acetate and water
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. washthe combined organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-91f3f5f6d5e247c3be5e5958504b93b6
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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