Acetic Acid → HCID 67608240, compound

HRID 1847113Notes

Reaction equation

HRID 1847113 reaction equation
[O:1]1[C@H:3]2[C:4](=O)[CH2:5][C@H:6]3[C@:26]([CH3:27])([C@@H:2]12)[C:25]1[CH2:24][CH2:23][C@@:22]2([CH3:28])[C@@H:10]([CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[C:9]=1[O:8][C:7]3=[O:29].O.NN.C(O)(=O)C.O>C(O)C>[OH:1][C@@H:2]1[C@@:26]2([CH3:27])[C@@H:6]([C:7](=[O:29])[O:8][C:9]3[C@H:10]4[C@:22]([CH3:28])([CH2:23][CH2:24][C:25]=32)[C@@H:13]([C@H:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:12][CH2:11]4)[CH2:5][CH:4]=[CH:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 50899674HCID 50899674, compound

Product 1

HCID 67608240HCID 67608240, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 6 (9.0 mg, 0.022 mmol) obtained in Example 5 was dissolved in ethanol (0.5 mL), and hydrazine monohydrate (10 μL) and acetic acid (10 μL) were added thereto at room temperature, followed by stirring for 1 hour. Water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to yield a residue. The residue was purified by preparative thin layer chromatography to obtain the title compound (6.2 mg, 71%).

Workup

  1. customat room temperature
  2. extractionfollowed by extraction with ethyl acetate twice
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto yield a residue
  7. customThe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-cf4145ca54dd4972b9f6b2024b0b8277
Source dataset
uspto-grants-2015_02
Patent number
US08952003B2

Reaction notes

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