Butanoic acid, 4-chloro-4-oxo-, methyl ester → HCID 18332963, compound

HRID 2269703Notes

Reaction equation

HRID 2269703 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][C:7](Cl)=[O:8])=[O:4].O[NH:11][C:12](=[NH:22])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1>C(#N)C.N1C=CC=CC=1.C(OCC)(=O)C>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C:12]2[N:11]=[C:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[O:8][N:22]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 2

HCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 178490401HCID 178490401, compound

Product 1

HCID 18332963HCID 18332963, compoundYield 54.4%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Methoxycarbonylpropionyl chloride (4.5 g) was added dropwise to a mixed solution of N-hydroxy-2-(4-methoxyphenyl)ethaneimidamide (3 g) in acetonitrile (20 ml) and pyridine (5 ml) under ice-cooling. The reaction mixture was stirred at room temperature for 3 hours, which was diluted with ethyl acetate. The reaction mixture was washed twice with 2N hydrochloric acid and water, then dried and concentrated. The obtained residue was dissolved in pyridine (20 ml) and stirred under heating at 100° C. for 18 hours. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/1) to obtain methyl 3-[3-(4-methoxyphenyl)methyl-1,2,4-oxadiazol-5-yl]propionate (2.5 g).

Workup

  1. temperaturecooling
  2. washThe reaction mixture was washed twice with 2N hydrochloric acid and water
  3. customdried
  4. concentrationconcentrated
  5. dissolutionThe obtained residue was dissolved in pyridine (20 ml)
  6. stirringstirred
  7. temperatureunder heating at 100° C. for 18 hours
  8. concentrationThe reaction mixture was concentrated
  9. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-eb524394a38c476eb0e3e3aba5d9278a
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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