Water → HCID 22344634, compound

HRID 2299852Notes

Reaction equation

HRID 2299852 reaction equation
[CH3:1][C:2]1O[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]2\[CH2:23][C:24]([CH:28]([CH3:32])C(O)=O)=[CH:25][CH:26]=[CH:27]\2)=[CH:17][CH:16]=1.Cl.C(N=C=NCCCN(C)C)C.C[N:48](C)[CH:49]=[O:50].[OH2:52]>>[CH3:1][C:2]1[O:52][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:16]=[CH:17][C:18]([CH2:19][O:20]/[N:21]=[C:22](/[C:27]2[CH:32]=[CH:28][CH:24]=[CH:25][CH:26]=2)\[CH2:23][C:49]([NH2:48])=[O:50])=[CH:33][CH:34]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 88184024HCID 88184024, compound

Product 1

HCID 22344634HCID 22344634, compoundYield 86%

Procedure

A mixture of E-3-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-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-a8a86b4e5f7c49d090da151410f12cfb
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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