Dimethylformamide → (4E)-N,N-dimethyl-4-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-4-phenylbutanamide

HRID 1070173Notes

Reaction equation

HRID 1070173 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][N:8]([CH3:11])[CH:9]=[O:10].[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(O)=O)=[CH:28][CH:27]=1.C(OCC)(=O)C.CCCCCC>O1CCCC1>[CH3:7][N:8]([CH3:11])[C:9](=[O:10])[CH2:35][CH2:34]/[C:33](=[N:32]\[O:31][CH2:30][C:29]1[CH:45]=[CH:46][C:26]([O:25][CH2:24][C:14]2[N:15]=[C:16]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[O:17][C:13]=2[CH3:12])=[CH:27][CH:28]=1)/[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 9890879ImiglitazarHCID 21226206Ethyl acetate hexane

Product 1

HCID 22344643(4E)-N,N-dimethyl-4-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-4-phenylbutanamideYield 69%

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 (5 ml) and added dropwise to a mixture of a 40% aqueous dimethylamine (20 ml) and ethyl acetate (20 ml) at 0° C. After stirred at room temperature for 2 hours, 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 residue was subjected to silica gel chromatography to obtain E-N,N-dimethyl-4-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-4-phenylbutanamide (511 mg, yield 69%) as a colorless oil from an ethyl acetate-hexane (2:1, v/v).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in tetrahydrofuran (5 ml)
  3. additionadded dropwise to a mixture of a 40% aqueous dimethylamine (20 ml) and ethyl acetate (20 ml) at 0° C
  4. stirringAfter stirred at room temperature for 2 hours
  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

Sources & evidence

ORD record
ord-7912b3b2ab354c95a810e167349a81a8
Source dataset
uspto-grants-2001_06
Patent number
US06251926B1

Reaction notes

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