Lithium Hydroxide → HCID 22482959, compound

HRID 1019414Notes

Reaction equation

HRID 1019414 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:20])[CH:11]([OH:19])[C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.Br[C:22]([CH3:29])([CH3:28])[C:23]([O:25]CC)=[O:24].C(=O)([O-])[O-].[K+].[K+].[OH-].[Li+]>CN(C)C=O.C(O)C.O>[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([CH:11]([OH:19])[C:12]2[CH:17]=[CH:16][C:15]([O:18][C:22]([CH3:29])([CH3:28])[C:23]([OH:25])=[O:24])=[CH:14][CH:13]=2)=[O:20])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

8

Reactant 4

HCID 3939Lithium HydroxideHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 18401127HCID 18401127, compound

Product 1

HCID 22482959HCID 22482959, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The preparation of the ethyl ester was carried out using N-(3,5-Dimethyl-phenyl)-2-hydroxy-2-(4-hydroxy-phenyl)acetamide (4.0 g, 14.8 mmol), ethyl 2-bromoisobutyrate (19.2 g, 19.2 mmol), potassium carbonate (3.0 g, 22.1 mmol) in dimethylformamide (30 mL) to yield 2.9 g after column chromatography purification. Hydrolysis of the ester was carried out with (1.0 g, mmol) in ethanol (40 mL) and lithium hydroxide (1.05 g, 25 mmol) dissolved in water (20 mL). Purification by column chromatography gave 900 mg. m.p.

Workup

  1. customto yield 2.9 g
  2. customafter column chromatography purification
  3. customHydrolysis of the ester
  4. customPurification by column chromatography
  5. customgave 900 mg

Sources & evidence

ORD record
ord-3dd85aaca39145fc8b9de28927260aa2
Source dataset
uspto-grants-2002_11
Patent number
US06486342B1

Reaction notes

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