Tetrahydrofuran → HCID 54413093, compound

HRID 1608322Notes

Reaction equation

HRID 1608322 reaction equation
[CH3:1][C:2]1[C:3](=[O:19])[NH:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([O:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O)=[CH:7][CH:6]=2.O1[CH2:24][CH2:23][CH2:22][CH2:21]1.C(Cl)(=O)[C:26]([CH3:29])(C)C.C1([CH2:38][CH2:39][NH2:40])CCCCC1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:1][C:2]1[C:3](=[O:19])[NH:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([O:12][CH2:13][CH2:14][CH2:15][C:16]([N:40]([CH:21]1[CH2:29][CH2:26][CH2:24][CH2:23][CH2:22]1)[CH2:39][CH3:38])=[O:18])=[CH:7][CH:6]=2

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 205092-CyclohexylethylamineHCID 62493Pivaloyl chlorideHCID 19849135HCID 19849135, compound

Product 1

HCID 54413093HCID 54413093, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

3-methyl-6-(3-carboxypropoxy)-2-oxo-1,2-dihydroquinoxaline 2.0 mM obtained in Example 11 was added to tetrahydrofuran 20 ml. An equimolar amount of triethylamine was added thereto, and there was further added dropwise an equimolar amount of pivaloyl chloride at -10° C. and the mixture was stirred at below -10° C. for 1 hour. N-cyclohexylethylamine 0.3 ml was added at once to the obtained reaction mixture, and the mixture was stirred for 3 hours while gradually adjusting the temperature to room temperature. Chloroform was added to the reaction mixture, and the mixture was washed with dilute aqueous potassium carbonate. The aqueous layer was further extracted with chloroform. The combined chloroform layers were dried by adding anhydrous sodium sulfate and concentrated in vacuo. The residue was charged on a column of silica gel (C-200, 70 g) and eluted with chloroform-methanol (50:1) to obtain the compound 1029.

Workup

  1. customonce to the obtained reaction mixture
  2. stirringthe mixture was stirred for 3 hours
  3. customto room temperature
  4. washthe mixture was washed with dilute aqueous potassium carbonate
  5. extractionThe aqueous layer was further extracted with chloroform
  6. dry with materialThe combined chloroform layers were dried
  7. additionby adding anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. additionThe residue was charged on a column of silica gel (C-200, 70 g)
  10. washeluted with chloroform-methanol (50:1)

Sources & evidence

ORD record
ord-aad30cf91e0440568bf35271c1323070
Source dataset
uspto-grants-1989_09
Patent number
US04870175

Reaction notes

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