Lithium Hydroxide → HCID 9838569, compound

HRID 1604438Notes

Reaction equation

HRID 1604438 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]([CH3:22])[C:18]([O:20]C)=[O:19])=[CH:13][CH:12]=1)=[CH:6][CH:5]=2.[Li+].[OH-]>C1COCC1.CO>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]([CH3:22])[C:18]([OH:20])=[O:19])=[CH:13][CH:12]=1)=[CH:6][CH:5]=2

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 19603851HCID 19603851, compound

Product 1

HCID 9838569HCID 9838569, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 16d (24 mg, 82 μmol) in THF (2 mL) and MeOH (0.5 mL) was added a 1.0N aqueous solution of LiOH (0.2 mL, 200 μmol) and the resulting mixture was stirred at room temperature overnight. The reaction was diluted with a 25% aqueous solution of NH4OAc and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. Purification by flash chromatography (30:70:1 EtOAc/hexane/AcOH) gave 23 mg of the title compound as a light yellow gum.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customPurification by flash chromatography (30:70:1 EtOAc/hexane/AcOH)

Sources & evidence

ORD record
ord-dfa696cc6b514c62af84ec962e25740a
Source dataset
uspto-grants-1999_11
Patent number
US05994379

Reaction notes

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