Sodium Hydroxide → HCID 21107126, compound

HRID 2377501Notes

Reaction equation

HRID 2377501 reaction equation
C[O:2][C:3](=[O:33])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[C:24]([CH3:25])=[CH:23][C:22]3[CH:21]([N:26]([CH:28]4[CH2:30][CH2:29]4)[CH3:27])[CH2:20][CH2:19][C:18]([CH3:32])([CH3:31])[C:17]=3[CH:16]=2)=[CH:9][CH:8]=1)([CH3:6])[CH3:5].[OH-].[Na+]>CO.O1CCCC1>[CH:28]1([N:26]([CH3:27])[CH:21]2[CH2:20][CH2:19][C:18]([CH3:31])([CH3:32])[C:17]3[CH:16]=[C:15]([C:14]#[C:13][C:10]4[CH:9]=[CH:8][C:7]([C:4]([CH3:6])([CH3:5])[C:3]([OH:33])=[O:2])=[CH:12][CH:11]=4)[C:24]([CH3:25])=[CH:23][C:22]2=3)[CH2:29][CH2:30]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69069738HCID 69069738, compound2×

Product 1

HCID 21107126HCID 21107126, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-{4-[5-(cyclopropyl-methyl-amino)-3,8,8-trimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-phenyl}-2-methyl-propionic acid methyl ester (Intermediate 175, 0.035 g, 0.08 mmol) in methanol (2 mL) and tetrahydrofuran (2 mL) was treated with a 2M solution of sodium hydroxide (2 mL, 4 mmol) and the resulting reaction mixture was refluxed for 2 days. The volatiles were evaporated in vacuo and the residue was neutralized with 5% aqueous hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a residue that was purified by preparative reverse phjase HPLC using 10% water in acetonitrile as the mobile phase to afford the title product (0.022 g, 64%).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 2 days
  3. customThe volatiles were evaporated in vacuo
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo to a residue that
  9. customwas purified by preparative reverse phjase HPLC

Sources & evidence

ORD record
ord-17a391ce83834337a9d2ef872b18ae21
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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