Lithium Hydroxide → HCID 58011789, compound

HRID 660880Notes

Reaction equation

HRID 660880 reaction equation
C[O:2][C:3](=[O:20])[CH2:4][N:5]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[C:7]([Br:19])=[N:6]1.[OH-].[Li+]>CO>[Br:19][C:7]1[N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[C:9](=[O:10])[N:5]([CH2:4][C:3]([OH:20])=[O:2])[N:6]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58011843HCID 58011843, compound

Product 1

HCID 58011789HCID 58011789, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound from Example 138A (360 mg) is dissolved in 10 ml methanol and treated with 4.2 ml of a 1 M aqueous lithium hydroxide solution. The mixture is stirred overnight at RT and then freed of methanol on the rotary evaporator. The residue is diluted with 200 ml water and slowly acidified to pH 2 with 1 N hydrochloric acid. The aqueous phase is extracted three times with ethyl acetate, the combined organic phases dried over sodium sulphate and the solvent removed on the rotary evaporator. The residue is dissolved in a little DMSO and purified by preparative HPLC (Method 20). 246 mg (0.75 mmol) of the title compound are obtained.

Workup

  1. customfreed of methanol on the rotary evaporator
  2. additionThe residue is diluted with 200 ml water
  3. extractionThe aqueous phase is extracted three times with ethyl acetate
  4. dry with materialthe combined organic phases dried over sodium sulphate
  5. customthe solvent removed on the rotary evaporator
  6. dissolutionThe residue is dissolved in a little DMSO
  7. custompurified by preparative HPLC (Method 20)

Sources & evidence

ORD record
ord-f4160b586e344e5facee8b1c818dc6e1
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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