Sodium Hydroxide → HCID 18331271, compound

HRID 2270098Notes

Reaction equation

HRID 2270098 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:9][CH2:8][CH:7]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][N:18]=3)[C:13](=[O:20])[C:12]([C:21]([O:23]CC)=[O:22])=[CH:11]2)[CH2:6]1)=[O:4].[OH-].[Na+]>O1CCCC1.C(O)C.O>[CH3:1][O:2][C:3]([N:5]1[CH2:9][CH2:8][CH:7]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][N:18]=3)[C:13](=[O:20])[C:12]([C:21]([OH:23])=[O:22])=[CH:11]2)[CH2:6]1)=[O:4]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 131723021HCID 131723021, compound

Product 1

HCID 18331271HCID 18331271, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of 269 mg (0.78 mmol) of the compound obtained in Example 2 in 3 ml of tetrahydrofuran and 3 ml of ethanol, 857 μl (0.857 mmol) of 1N sodium hydroxide solution was added at room temperature and the solution was stirred at that temperature for 1.5 hours. Next, this was diluted with water (20 ml) and, after washing with ether (10 ml), 1N hydrochloric acid (0.87 ml) was added to an aqueous layer. After extracting with methylene chloride (40 ml), the extract was dried over anhydrous sodium sulfate, then the solvent was distilled off under vacuum. Thus, 237 mg (96%) of the above-identified compound was obtained as a slightly yellow crystal.

Workup

  1. washafter washing with ether (10 ml), 1N hydrochloric acid (0.87 ml)
  2. additionwas added to an aqueous layer
  3. extractionAfter extracting with methylene chloride (40 ml)
  4. dry with materialthe extract was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under vacuum

Sources & evidence

ORD record
ord-7da77b6667a8403bbcc69548aec53b45
Source dataset
uspto-grants-2001_12
Patent number
US06331548B1

Reaction notes

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