Lithium hydroxide, monohydrate → HCID 59404863, compound

HRID 1929796Notes

Reaction equation

HRID 1929796 reaction equation
[C:1]([N:5]1[CH2:10][CH2:9][C@@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][C:21]=2[O:22][CH3:23])[N:18]=[CH:17][N:16]=[C:15]3[NH:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[C:27]([Cl:32])[C:26]=2[F:33])[CH2:7][C@@H:6]1[C:34]([O:36]C)=[O:35])(=[O:4])[CH:2]=[CH2:3].O.[OH-].[Li+]>O1CCCC1.CO>[C:1]([N:5]1[CH2:10][CH2:9][C@@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][C:21]=2[O:22][CH3:23])[N:18]=[CH:17][N:16]=[C:15]3[NH:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[C:27]([Cl:32])[C:26]=2[F:33])[CH2:7][C@@H:6]1[C:34]([OH:36])=[O:35])(=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59404841HCID 59404841, compound

Product 1

HCID 59404863HCID 59404863, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

15 mg of the compound obtained in Example 133 was dissolved in 0.2 ml of a mixed solvent of tetrahydrofuran and methanol (1:1), and 1.4 mg of lithium hydroxide monohydrate was added thereto at 0° C. The resulting mixture was incubated at room temperature for one hour. After the reaction terminated, the resulting solution was acidified to pH 4 with a 3N HCl and extracted twice with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate, filtered and distilled under a reduced pressure. The resulting residue was purified by column chromatography (methylene chloride:ethyl acetate:methanol=1:1:1) to obtain the title compound (10 mg, 69%).

Workup

  1. additionwas added
  2. customat 0° C
  3. customAfter the reaction terminated
  4. extractionextracted twice with methylene chloride
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. distillationdistilled under a reduced pressure
  8. customThe resulting residue was purified by column chromatography (methylene chloride:ethyl acetate:methanol=1:1:1)

Sources & evidence

ORD record
ord-f251c198568d4388a00e64ecf8dda707
Source dataset
uspto-grants-2012_05
Patent number
US08188102B2

Reaction notes

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