Acetic Acid → HCID 178439051, compound

HRID 1064839Notes

Reaction equation

HRID 1064839 reaction equation
C[N:2](C)[CH:3]=[CH:4][C:5]([C:7]1[C:15]2[O:14][C:13]([S:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][N:22]([CH2:25][C:26]([NH:28][C:29]4[C:34]([CH:35]([CH3:37])[CH3:36])=[CH:33][CH:32]=[CH:31][C:30]=4[CH:38]([CH3:40])[CH3:39])=[O:27])[CH2:21][CH2:20]3)=[N:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)=O.C(O)(=O)C.O.[NH2:47]N>CO>[NH:2]1[CH:3]=[CH:4][C:5]([C:7]2[C:15]3[O:14][C:13]([S:16][CH2:17][CH2:18][N:19]4[CH2:20][CH2:21][N:22]([CH2:25][C:26]([NH:28][C:29]5[C:34]([CH:35]([CH3:37])[CH3:36])=[CH:33][CH:32]=[CH:31][C:30]=5[CH:38]([CH3:40])[CH3:39])=[O:27])[CH2:23][CH2:24]4)=[N:12][C:11]=3[CH:10]=[CH:9][CH:8]=2)=[N:47]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 69731813HCID 69731813, compound

Product 1

HCID 178439051HCID 178439051, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the enamine (245 mg, 0.4 mmol) in methanol (6 ml) were added acetic acid (123 mg, 2.05 mmol) and hydrazine monohydrate (102 mg, 2.05 mmol) followed by stirring at room temperature for 15 hours. The reaction solution was concentrated and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution, dried over sodium sulfate and the solvent was evaporated therefrom. The residue was purified by a preparative thin layer chromatography (developing solvent, hexane:acetone=5:3) to provide 129 mg (yield 58%) of the desired compound as colorless needles.

Workup

  1. concentrationThe reaction solution was concentrated
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated sodium chloride solution, dried over sodium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by a preparative thin layer chromatography (developing solvent, hexane:acetone=5:3)

Sources & evidence

ORD record
ord-0895b4cc93db4cd0ae971a62658a76fc
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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