Sodium Hydroxide → HCID 69072342, compound

HRID 1765873Notes

Reaction equation

HRID 1765873 reaction equation
C([O:3][C:4](=[O:35])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:24]=[C:23]([CH:25]3[CH2:27][CH2:26]3)[C:22]3[CH:21]([N:28]([CH:30]4[CH2:32][CH2:31]4)[CH3:29])[CH2:20][CH2:19][C:18]([CH3:34])([CH3:33])[C:17]=3[CH:16]=2)=[CH:9][CH:8]=1)C.[OH-].[Na+]>CO.O1CCCC1>[CH:25]1([C:23]2[C:22]3[CH:21]([N:28]([CH:30]4[CH2:31][CH2:32]4)[CH3:29])[CH2:20][CH2:19][C:18]([CH3:33])([CH3:34])[C:17]=3[CH:16]=[C:15]([C:14]#[C:13][C:10]3[CH:9]=[CH:8][C:7]([CH:6]=[CH:5][C:4]([OH:35])=[O:3])=[CH:12][CH:11]=3)[CH:24]=2)[CH2:27][CH2:26]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69075690HCID 69075690, compound2×

Product 1

HCID 69072342HCID 69072342, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-{4-[4-cyclopropyl-5-(cyclopropyl-methyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-phenyl}-acrylic acid ethyl ester (Intermediate 164, 0.08 g, 0.17 mmol) in methanol (3 mL) and tetrahydrofuran (3 mL) was treated with 2M sodium hydroxide solution (2 mL, 4 mmol) and the resulting reaction mixture was refluxed overnight. The reaction mixture was cooled to ambient temperature, the volatiles were evaporated in vacuo, the residue was diluted with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate (×2). The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a solid. Preparative reverse phase HPLC using 10% water in acetonitrile as the mobile phase afforded the title product as a solid (0.04 g, 50%).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed overnight
  3. customthe volatiles were evaporated in vacuo
  4. additionthe residue was diluted with saturated aqueous ammonium chloride solution
  5. extractionextracted with ethyl acetate (×2)
  6. extractionThe combined organic extract
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo to a solid

Sources & evidence

ORD record
ord-c0b336f20b6a4b85966178cfd0bf03f2
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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