Lithium Hydroxide → Gavestinel

HRID 1492158Notes

Reaction equation

HRID 1492158 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH:15]=[CH:16][C:17](=[O:25])[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[C:12]([Cl:26])[CH:11]=[C:10]([Cl:27])[CH:9]=2)=[O:5])C.[OH-].[Li+]>C(O)C>[C:19]1([NH:18][C:17](/[CH:16]=[CH:15]/[C:14]2[C:13]3[C:8](=[CH:9][C:10]([Cl:27])=[CH:11][C:12]=3[Cl:26])[NH:7][C:6]=2[C:4]([OH:5])=[O:3])=[O:25])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 53759569HCID 53759569, compound

Product 1

HCID 6450546GavestinelYield 98.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Example 1 (250 mg) in ethanol (2.5 ml), lithium hydroxide (104 mg) was added at 23°. The reaction was stirred at 50° for 6 hours then the solvent was evaporated and the residue dissolved in water (5 ml). The aqueous layer was acidified with 1N hydrochloric acid until a white solid precipitated. The latter was collected by filtration and dried to give the title compound as a white solid (230 mg).

Workup

  1. customthe solvent was evaporated
  2. dissolutionthe residue dissolved in water (5 ml)
  3. customprecipitated
  4. filtrationThe latter was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-fe1c2102429244d1b95bfb822b3b2d65
Source dataset
uspto-grants-1994_12
Patent number
US05373018

Reaction notes

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