Sodium Hydroxide → HCID 136000719, compound

HRID 915936Notes

Reaction equation

HRID 915936 reaction equation
[CH:1]1([C:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12]([C:17]4[CH:22]=[CH:21][C:20]([S:23]([N:26]5[CH2:31][CH2:30][CH:29]([C:32]([O:34]CC)=[O:33])[CH2:28][CH2:27]5)(=[O:25])=[O:24])=[CH:19][C:18]=4[O:37][CH3:38])=[N:11][C:10]=3[N:9]([CH3:39])[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([C:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12]([C:17]4[CH:22]=[CH:21][C:20]([S:23]([N:26]5[CH2:27][CH2:28][CH:29]([C:32]([OH:34])=[O:33])[CH2:30][CH2:31]5)(=[O:25])=[O:24])=[CH:19][C:18]=4[O:37][CH3:38])=[N:11][C:10]=3[N:9]([CH3:39])[N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136005805HCID 136005805, compound

Product 1

HCID 136000719HCID 136000719, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 2 ml methanol/3 ml tetrahydrofuran mixed solution of 82 mg (0.15 mmol) of the compound obtained in Example 53, 1 ml (1 mmol) of a 1M aqueous solution of sodium hydroxide was added, and the mixture was stirred at room temperature for 1 hour. Then, the solvent was distilled off under reduced pressure, and the residue was diluted with water. The aqueous layer was washed with ether, then acidified with a 2M aqueous solution of hydrochloric acid, and extracted with dichloromethane. 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 to obtain 77 mg (99%) of the captioned compound.

Workup

  1. distillationThen, the solvent was distilled off under reduced pressure
  2. additionthe residue was diluted with water
  3. washThe aqueous layer was washed with ether
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with water
  6. dry with materialAfter the washed layer was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e73dbc0f814b44009607ca1402b09da9
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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