Sodium Hydroxide → HCID 68775846, compound

HRID 2191089Notes

Reaction equation

HRID 2191089 reaction equation
[OH-].[Na+].[CH3:3][C:4]1([CH3:34])[CH2:32][C:8]2[C:9]([C:18]3[CH:19]=[C:20]([NH:24][C:25](=[O:31])[C:26]([O:28]CC)=[O:27])[CH:21]=[CH:22][CH:23]=3)=[C:10]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[S:11][C:7]=2[C:6](=[O:33])[CH2:5]1>C1COCC1.O>[CH3:3][C:4]1([CH3:34])[CH2:32][C:8]2[C:9]([C:18]3[CH:19]=[C:20]([NH:24][C:25](=[O:31])[C:26]([OH:28])=[O:27])[CH:21]=[CH:22][CH:23]=3)=[C:10]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[S:11][C:7]=2[C:6](=[O:33])[CH2:5]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 90914169HCID 90914169, compound

Product 1

HCID 68775846HCID 68775846, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (53 mg, 1.32 mmol) was added to a mixture of Example 256 (300 mg, 0.66 mmol) in THF (10 mL) and water (10 mL) and the reaction mixture was stirred at room temperature for 3 h. The THF was removed in vacuo and the aqueous phase was diluted with water (10 mL), washed with EtOAc (20 mL) and acidified to pH 2 with 2M aqueous HCl. The aqueous phase was extracted with EtOAc (50 mL) and the organic phase was dried (magnesium sulfate) and the solvent was removed in vacuo to give the title compound (204 mg, 72%) as a yellow solid. δH (CDCl3) 9.04 (1H, br s), 7.77-7.74 (1H, m), 7.59-7.47 (2H, m), 7.28-7.25 (1H, m), 3.72-3.66 (4H, m), 3.04-2.98 (4H, m), 2.51 (2H, s), 2.47 (2H, s), 1.06 (6H, s). LCMS (ES+) 429.0 (M+H)+.

Workup

  1. customThe THF was removed in vacuo
  2. additionthe aqueous phase was diluted with water (10 mL)
  3. washwashed with EtOAc (20 mL)
  4. extractionThe aqueous phase was extracted with EtOAc (50 mL)
  5. dry with materialthe organic phase was dried (magnesium sulfate)
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-213bcfaaea844231badddbe9d6f2fa79
Source dataset
uspto-grants-2012_12
Patent number
US08324204B2

Reaction notes

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