Ethyl Acetate → HCID 23122046, compound

HRID 1713566Notes

Reaction equation

HRID 1713566 reaction equation
[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]3[CH2:12][NH:13][CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:24][C:25]([N:27]=[C:28]=[O:29])=[O:26].[NH:30]1[CH2:35][CH:34]=[CH:33][CH2:32][CH2:31]1.C(OCC)(=O)C>O1CCCC1>[N:30]1([CH2:24][C:25]([NH:27][C:28]([N:13]2[CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8][C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:11]3[CH2:12]2)=[O:29])=[O:26])[CH2:31][CH:32]=[CH:33][CH2:34][CH2:35]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 127501,2,3,6-TetrahydropyridineHCID 78209Chloroacetyl isocyanateHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 23122046HCID 23122046, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

Hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (0.22 g, 0.75 mmol) was dissolved in tetrahydrofuran (7.5 mL). 2-Chloroacetyl isocyanate (0.10 g, 0.83 mmol) was added thereto, and the mixture was stirred at −20° C. for 1 hour. 1,2,3,6-Tetrahydropyridine (0.27 mL, 3.0 mmol) was added thereto, and the mixture was stirred at room temperature for 24 hours. To the reaction solution was added ethyl acetate, and the resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate), and then crystallized from ethyl acetate-hexane to obtain the title compound (0.25 g, yield 72%).

Workup

  1. stirringthe mixture was stirred at room temperature for 24 hours
  2. washthe resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate)
  6. customcrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-2663997350aa483fa83612ed199f1feb
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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