Oxalyl chloride → HCID 23121945, compound

HRID 1713521Notes

Reaction equation

HRID 1713521 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[C:19]1([C:25]2([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:29]3[CH2:30][NH:31][CH2:32][CH2:33][N:28]3[C:27](=[O:34])[O:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])O.[Na+]>O1CCCC1.CN(C)C=O.C(N(C(C)C)CC)(C)C>[F:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:6]=[CH:7]/[C:8]([N:31]2[CH2:32][CH2:33][N:28]3[C:27](=[O:34])[O:26][C:25]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:29]3[CH2:30]2)=[O:10])=[CH:11][CH:12]=1

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 980703-(4-Fluorophenyl)-2-propenoic acidHCID 516892Sodium BicarbonateHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 23121945HCID 23121945, compoundYield 36.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of 4-fluorocinnamic acid (50 mg, 0.30 mmol) in tetrahydrofuran (1 mL) were sequentially added oxalyl chloride (46 mg, 0.36 mmol) and N,N-dimethylformamide (one drop), and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure. A solution of hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (60 mg, 0.20 mmol) in tetrahydrofuran (1.5 mL) and diisopropylethylamine (0.3 mL) were sequentially added thereto, and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added an aqueous saturated sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1) and crystallized from ethyl acetate-diisopropyl ether to obtain the title compound (32 mg, yield 36%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. stirringthe mixture was stirred at room temperature for 3 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1)
  7. customcrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-3172fbf0764a4a8080b8aeed8dabf29d
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

Loading…