Triethylamine → HCID 131720258, compound

HRID 1490017Notes

Reaction equation

HRID 1490017 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O.C(N(CC)CC)C.[C:23]([O:27][C:28](=[O:31])[NH:29][NH2:30])([CH3:26])([CH3:25])[CH3:24]>O1CCCC1>[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([NH:30][NH:29][C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:31])=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69957Monomethyl sebacateHCID 70091tert-Butyl carbazate

Product 1

HCID 131720258HCID 131720258, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

10.81 g (50 mmol) of sebacic acid monomethyl ester is dissolved in tetrahydrofuran and successively mixed with 8.32 ml (60 mmol) of triethylamine and 5.28 ml (55 mmol) of chloroformic acid ethyl ester [ethyl chloroformate] at -5° C.. After 15 minutes 6.61 g (50 mmol) of tert-butylcarbazate in tetrahydrofuran is instilled at this temperature and then stirred at room temperature for 2 hours. The precipitate is suctioned off, the filtrate is concentrated by evaporation and taken up in ethyl acetate. The organic phase is successively washed with NaHCO3 solution, citric acid and water and dried on Na2SO4. The oil obtained after concentration by evaporation of the ethyl acetate is chromatographed on silica gel in diisopropyl ether.

Workup

  1. concentrationthe filtrate is concentrated by evaporation
  2. washThe organic phase is successively washed with NaHCO3 solution, citric acid and water
  3. customdried on Na2SO4
  4. customThe oil obtained
  5. concentrationafter concentration
  6. customby evaporation of the ethyl acetate
  7. customis chromatographed on silica gel in diisopropyl ether

Sources & evidence

ORD record
ord-4c86d102f04f4632b6ab15ea9e8a175b
Source dataset
uspto-grants-1997_10
Patent number
US05681544

Reaction notes

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