Lithium Hydroxide → HCID 21107163, compound

HRID 2377531Notes

Reaction equation

HRID 2377531 reaction equation
C([O:3][C:4](=[O:32])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([NH:14][C:15]2[CH:16]=[C:17]3[C:22](=[C:23]([C:25]#[CH:26])[CH:24]=2)[O:21][C:20]([CH3:28])([CH3:27])[CH2:19][C:18]3([CH3:30])[CH3:29])=[O:13])=[CH:7][C:6]=1[F:31])C.[OH-].[Li+]>CO.O1CCCC1.O>[C:25]([C:23]1[CH:24]=[C:15]([NH:14][C:12](=[O:13])[NH:11][C:8]2[CH:9]=[CH:10][C:5]([C:4]([OH:32])=[O:3])=[C:6]([F:31])[CH:7]=2)[CH:16]=[C:17]2[C:22]=1[O:21][C:20]([CH3:27])([CH3:28])[CH2:19][C:18]2([CH3:30])[CH3:29])#[CH:26]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 57424275HCID 57424275, compound2×

Product 1

HCID 21107163HCID 21107163, compoundYield 62.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[3-(8-ethynyl-2,2,4,4-tetramethyl-chroman-6-yl)-ureido]-2-fluoro-benzoic acid ethyl ester (Intermediate 212, 0.12 g) in methanol (2 mL), tetrahydrofuran (2 mL) and water (1 mL) was treated with lithium hydroxide (0.177 g, 4.2 mmol) and the resulting reaction mixture was stirred at ambient temperature overnight. The volatiles were evaporated in vacuo, the residue was diluted with water and neutralized with dilute hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated to afford the title compound as a solid (0.07 g, 46% for two steps).

Workup

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo
  3. additionthe residue was diluted with water and neutralized with dilute hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-543e62d6e100450fbaf01c82b3266671
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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