Dimethylformamide → HCID 22344634, compound

HRID 584498Notes

Reaction equation

HRID 584498 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:34]=[CH:33][C:18]([CH2:19][O:20]/[N:21]=[C:22](/[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)\[CH2:23][C:24]([OH:26])=O)=[CH:17][CH:16]=1.Cl.C([N:38]=C=NCCCN(C)C)C.CN(C)C=O>O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][O:20]/[N:21]=[C:22](/[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)\[CH2:23][C:24]([NH2:38])=[O:26])=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10863408HCID 10863408, compound

Product 1

HCID 22344634HCID 22344634, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of E-3-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-3-phenylpropionic acid (600 mg), 1-hydroxybenzotriazole ammonia complex (260 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (328 mg) and N,N-dimethylformamide (5 ml) was stirred at room temperature for 15 hours. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed successively with an aqueous solution of potassium carbonate and an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The remaining crystals were recrystallized from tetrahydrofuran-hexane to obtain E-3-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-3-phenylpropanamide (512 mg, yield 86%) as colorless crystals. m.p. 164-165° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed successively with an aqueous solution of potassium carbonate
  3. dry with materialan aqueous saturated solution of sodium chloride, dried (MgSO4)
  4. concentrationconcentrated
  5. customThe remaining crystals were recrystallized from tetrahydrofuran-hexane

Sources & evidence

ORD record
ord-a975d70490254f0185d123c869e71cd6
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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