Succinic anhydride → Tetrahydro-gamma,3-dioxo-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazine-7(1H)-butanoic acid

HRID 1713548Notes

Reaction equation

HRID 1713548 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.C(N(CC)CC)C.[C:30]1(=[O:36])[O:35][C:33](=[O:34])[CH2:32][CH2:31]1.C(OCC)(=O)C>O1CCCC1>[O:36]=[C:30]([N:13]1[CH2:14][CH2:15][N:10]2[C:9](=[O:16])[O:8][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:11]2[CH2:12]1)[CH2:31][CH2:32][C:33]([OH:35])=[O:34]

Participants

6

Reactant 4

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 23121918Tetrahydro-gamma,3-dioxo-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazine-7(1H)-butanoic acidYield 50.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (0.15 g, 0.50 mmol) in tetrahydrofuran (10 mL) were added triethylamine (0.14 mL, 1.0 mmol) and succinic anhydride (55 mg, 0.55 mmol), and the mixture was stirred at room temperature for 2 hours. To the reaction solution was added ethyl acetate, and the resulting mixture was washed with 2 M hydrochloric acid, 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). The fractions were concentrated, and to the residue was added diethyl ether. The resulting crystals were collected by filtration and washed with diethyl ether to obtain the title compound (99 mg, yield 50%).

Workup

  1. washthe resulting mixture was washed with 2 M hydrochloric acid
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate)
  5. concentrationThe fractions were concentrated
  6. additionto the residue was added diethyl ether
  7. filtrationThe resulting crystals were collected by filtration
  8. washwashed with diethyl ether

Sources & evidence

ORD record
ord-94c08ae51ee84b299b273528f54bdb15
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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