Chloroform → HCID 59398263, compound

HRID 39693Notes

Reaction equation

HRID 39693 reaction equation
C(Cl)(Cl)Cl.[CH3:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([N:11]=[CH:12][C:13](=[O:38])[N:14]2[CH2:17][CH2:18][CH2:19][C:20]2([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]2)=[CH:9][CH:8]=1.FC(F)(F)C(O)=O.C(OCC)(=O)C>O>[CH3:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([N:11]=[CH:12][C:13](=[O:38])[N:14]2[CH2:17][CH2:18][CH2:19][C:20]2([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 593978851-Tert-butyl 4-ethyl 4-(3-(7-methoxy-2-oxo-1,2-dihydroquinoxalin-1-yl)propyl)piperidine-1,4-dicarboxylate

Product 1

HCID 59398263HCID 59398263, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3.0 mL of a chloroform solution containing 0.60 g of 1-tert-butyl 4-ethyl 4-(3-(7-methoxy-2-oxo-1,2-dihydroquinoxalin-1-yl)propyl)piperidine-1,4-dicarboxylate, 1.5 mL of trifluoroacetic acid was added under cooling with ice, and the mixture was stirred at room temperature for 1 hour and 30 minutes. Thereto were added ethyl acetate and water. The aqueous layer was separated, ethyl acetate was added thereto, and the resultant solution was adjusted to pH 11.0 with a 20% aqueous saturated sodium hydroxide solution. The organic layer was separated, and washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 0.21 g of a pale yellow oily substance, ethyl 4-(3-(7-methoxy-2-oxo-1,2-dihydroquinoxalin-1-yl)propyl)piperidine-4-carboxylate.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. customThe aqueous layer was separated
  4. additionethyl acetate was added
  5. customThe organic layer was separated
  6. washwashed with an aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f622ba03de8d4da5a1b51fd6f6ee0b20
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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