Ethanol → HCID 136005830, compound

HRID 915921Notes

Reaction equation

HRID 915921 reaction equation
C(O)C.[CH:4]1([N:10]2[C:14]([C:15]([NH2:17])=[O:16])=[C:13]([NH:18][C:19](=O)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:26][CH3:27])[C:12]([CH3:29])=[N:11]2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[OH-].[Na+]>O>[CH:4]1([N:10]2[C:14]3[C:15](=[O:16])[NH:17][C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH3:27])=[N:18][C:13]=3[C:12]([CH3:29])=[N:11]2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 58959314HCID 58959314, compound

Product 1

HCID 136005830HCID 136005830, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a 2 ml ethanol solution of 100 mg (0.28 mmol) of the compound obtained in Example 9, 1 ml of a 1M aqueous solution of sodium hydroxide was added, and the mixture was stirred at 90° C. for 10 hours. Then, the reaction mixture was brought to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride. After the washed layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to obtain 68.5 mg (72%) of the captioned compound.

Workup

  1. customwas brought to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialAfter the washed layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-f973102f91d24998a006e063417704a7
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

Loading…