Lithium hydroxide, monohydrate → HCID 21083998, compound

HRID 347932Notes

Reaction equation

HRID 347932 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:15](=[O:16])[CH:14]=[CH:13][C:12]2[C:17]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:18]([C:20]([O:22]CC)=[O:21])[S:19][C:11]1=2)([O-:3])=[O:2].O.[OH-].[Li+]>O1CCOCC1.O>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:15](=[O:16])[CH:14]=[CH:13][C:12]2[C:17]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:18]([C:20]([OH:22])=[O:21])[S:19][C:11]1=2)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21084046HCID 21084046, compound

Product 1

HCID 21083998HCID 21083998, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of the compound of Example 120 (150 mg, 0.357 mmol) and lithium hydroxide monohydrate (30 mg, 0.714 mmol) in dioxane (3 mL) and water (3 mL) was heated under reflux for 1.5 h. The dioxane was removed in vacuo, the aqueous residue acidified (2M HCl) and the precipitate filtered off and dried to give the title compound as a pale orange solid (112 mg, 80%). δH (DMSO-d6) 13.06 (1H, br s), 8.29 (1H, dd, J 1.3, 8.2 Hz), 8.02–7.93 (2H, m), 7.88–7.84 (1H, m), 7.46–7.35 (6H, m), 6.46 (1H, d, J 9.7 Hz). LCMS (ES+) RT 3.137 minutes, 393.0 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 h
  3. customThe dioxane was removed in vacuo
  4. filtrationthe precipitate filtered off
  5. customdried

Sources & evidence

ORD record
ord-634cb3a1348943ea90669a09f59df4fd
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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