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

HRID 584493Notes

Reaction equation

HRID 584493 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 stirring 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 stirring 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-dc34390c0113490491f4b1dbe55fbde3
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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