Triethylamine → HCID 14837272, compound

HRID 2248364Notes

Reaction equation

HRID 2248364 reaction equation
Cl.[CH2:2]([O:5][C:6](=[O:16])[C@H:7]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH2:8])[CH2:3][CH3:4].C(N(CC)CC)C.[Cl:24][C:25]1=[C:26]([Cl:32])[C:27]([O:29][C:30]1=O)=[O:28]>O1CCCC1.C(O)(=O)C>[Cl:24][C:25]1[C:30](=[O:29])[N:8]([C@@H:7]([CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:6]([O:5][CH2:2][CH2:3][CH3:4])=[O:16])[C:27](=[O:28])[C:26]=1[Cl:32]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 70728Dichloromaleic anhydrideHCID 13783234HCID 13783234, compound

Product 1

HCID 14837272HCID 14837272, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

The hydrochloride thus obtained (1.0 g) was dissolved in 25 ml of tetrahydrofuran and allowed to react with 1.2 ml of triethylamine at room temperature for 30 minutes, the precipitated crystals were separated by filtration, and the filtrate concentrated under a reduced pressure to give a colorless oily product. This oily product and 700 mg of dichloromaleic anhydride were dissolved in 6 ml of acetic acid and refluxed for 3 hours, and after completion of the reaction, the reaction mixture was concentrated under a reduced pressure, the residue was dissolved in ethyl acetate, washed with water, and dried over magnesium sulfate, followed by evaporation of the solvent. The residue obtained was purified by silica gel chromatography (eluant: n-hexane-ethyl acetate=9/1) to give 1.41 g of the desired compound as a colorless oily product (yield: 97%).

Workup

  1. customthe precipitated crystals were separated by filtration
  2. concentrationthe filtrate concentrated under a reduced pressure
  3. customto give a colorless oily product
  4. temperaturerefluxed for 3 hours
  5. customafter completion of the reaction
  6. concentrationthe reaction mixture was concentrated under a reduced pressure
  7. dissolutionthe residue was dissolved in ethyl acetate
  8. washwashed with water
  9. dry with materialdried over magnesium sulfate
  10. customfollowed by evaporation of the solvent
  11. customThe residue obtained
  12. customwas purified by silica gel chromatography (eluant: n-hexane-ethyl acetate=9/1)

Sources & evidence

ORD record
ord-6f827aa7dc5b4828ad15a50ed6edc295
Source dataset
uspto-grants-1991_08
Patent number
US05039696

Reaction notes

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