Sodium Hydroxide → HCID 21107248, compound

HRID 2377356Notes

Reaction equation

HRID 2377356 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([CH2:16][N:17]([CH:21]3[CH2:23][CH2:22]3)[CH:18]([CH3:20])[CH3:19])[CH:15]=1)[O:12][C:11]([CH3:25])([CH3:24])[CH2:10][C:9]2([CH3:27])[CH3:26])=[O:5])C.[OH-].[Na+]>C(O)C.O1CCCC1>[CH:21]1([N:17]([CH2:16][C:14]2[CH:15]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[C:8]3[C:13]=2[O:12][C:11]([CH3:24])([CH3:25])[CH2:10][C:9]3([CH3:27])[CH3:26])[CH:18]([CH3:20])[CH3:19])[CH2:23][CH2:22]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57424222HCID 57424222, compound2×

Product 1

HCID 21107248HCID 21107248, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-[(cyclopropyl-isopropyl-amino)-methyl]-2,2,4,4-tetramethyl-chroman-6-carboxylic acid ethyl ester (Intermediate 38, 0.09 g, 0.26 mmol) in ethanol (3 mL) and tetrahydrofuran (1 mL) was treated with a 1M solution of sodium hydroxide (3 mL, 3 mmol) and the resulting reaction mixture was stirred at ambient temperature overnight. The volatiles were evaporated in vacuo, the residue was neutralized with dilute hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with water and brine and dried over anhydrous sodium sulfate, filtered and evaporated to afford the title compound (0.079 g, 96%). It was used as such for the next step.

Workup

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-393e8167367a413482efd0dde752cf08
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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