Triethylamine → HCID 70236198, compound

HRID 1068536Notes

Reaction equation

HRID 1068536 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:12])[C@H:5]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[NH2:6].Cl.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl.O>[CH3:2][O:3][C:4](=[O:12])[C@H:5]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[NH:6][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2734892L-Aspartic acid, 1,4-dimethyl ester, hydrochloride (1:1)HCID 12262826Isonicotinoyl chloride hydrochloride

Product 1

HCID 70236198HCID 70236198, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of L-aspartic acid dimethyl ester hydrochloride (2.0 g, 10 mmol) in chloroform (100 mL) was added isonicotinoyl chloride hydrochloride (1.8 g, 10 mmol) and triethylamine (3.0 mL, 21.5 mmol). The reaction mixture was refluxed for 2 h, and then stirred at room temperature for 24 h. The solution was filtered and the filtrate was evaporated to give a whitish oil. This residue was dissolved in 20 mL H2O, and was then extracted with ethyl acetate (2×100 mL). The organic phases were combined, washed with H2O (50 mL), and dried over Na2SO4. Removal of ethyl acetate gave a whitish oil, isonicotinoyl aspartic acid dimethyl ester. Electrospray MS: m/z=267 (M+1, [C12H14N2O5]+) 1H NMR (CDCl3): 2.91-3.17 (m, 2H, CH2), 3.69 (s, 3H, COOCH3), 3.78 (s, 3H, COOCH3), 4.99-5.05 (m, 1H, CH), 7.38-7.41 (d, 1H, NH), 7.62-7.65 (m, 2H, py), 7.82-7.84 (m, 2H, py).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. filtrationThe solution was filtered
  3. customthe filtrate was evaporated
  4. customto give a whitish oil
  5. extractionwas then extracted with ethyl acetate (2×100 mL)
  6. washwashed with H2O (50 mL)
  7. dry with materialdried over Na2SO4
  8. customRemoval of ethyl acetate

Sources & evidence

ORD record
ord-3b58590174414c47aa0c9d67e6c1aa08
Source dataset
uspto-grants-2001_06
Patent number
US06251364B1

Reaction notes

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