Dimethylformamide → Z-4-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-4-phenylbutanamide

HRID 2299847Notes

Reaction equation

HRID 2299847 reaction equation
C(Cl)(=O)C(Cl)=O.C[N:8](C)C=O.[CH3:12][C:13]1[O:17][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:15][C:14]=1[CH2:24][O:25][C:26]1[CH:46]=[CH:45][C:29]([CH2:30][O:31]/[N:32]=[C:33](/[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)\[CH2:34][CH2:35][C:36]([OH:38])=O)=[CH:28][CH:27]=1>O1CCCC1>[CH3:12][C:13]1[O:17][C:16]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[N:15][C:14]=1[CH2:24][O:25][C:26]1[CH:46]=[CH:45][C:29]([CH2:30][O:31]/[N:32]=[C:33](/[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)\[CH2:34][CH2:35][C:36]([NH2:8])=[O:38])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 9890879Imiglitazar

Product 1

HCID 12074180Z-4-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-4-phenylbutanamideYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Oxalyl chloride (0.156 ml) and N,N-dimethylformamide (catalytic amount) were added to a solution of E-4-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-4-phenylbutyric acid (700 mg) in tetrahydrofuran (10 ml) at room temperature, which was stirred at room temperature for 30 minutes and concentrated. The residue was dissolved in tetrahydrofuran (10 ml) and added dropwise to a mixture of a 25% aqueous ammonia (15 ml) and ethyl acetate (20 ml) at 0° C. After stirred at room temperature for 1 hour, water was added and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The remaining crystals were recrystallized from ethyl acetate to obtain E-4-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-4-phenylbutyramide (315 mg, yield 45%) as colorless crystals. m.p. 164-165° C.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in tetrahydrofuran (10 ml)
  3. additionadded dropwise to a mixture of a 25% aqueous ammonia (15 ml) and ethyl acetate (20 ml) at 0° C
  4. stirringAfter stirred at room temperature for 1 hour
  5. additionwater was added
  6. extractionextracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe remaining crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f1ae9ee27a1044678dbc5b18261b27e9
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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