Potassium Hydroxide → HCID 21107127, compound

HRID 1870024Notes

Reaction equation

HRID 1870024 reaction equation
C[O:2][C:3](=[O:34])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:24]=[C:23]([CH2:25][CH3:26])[C:22]3[CH:21]([N:27]([CH:29]4[CH2:31][CH2:30]4)[CH3:28])[CH2:20][CH2:19][C:18]([CH3:33])([CH3:32])[C:17]=3[CH:16]=2)=[CH:9][CH:8]=1)([CH3:6])[CH3:5].[OH-].[K+].[Cl-].[NH4+]>CO.O1CCCC1>[CH:29]1([N:27]([CH3:28])[CH:21]2[CH2:20][CH2:19][C:18]([CH3:32])([CH3:33])[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:34])=[O:2])=[CH:12][CH:11]=4)[CH:24]=[C:23]([CH2:25][CH3:26])[C:22]2=3)[CH2:30][CH2:31]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 69072150HCID 69072150, compound2×

Product 1

HCID 21107127HCID 21107127, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-{4-[5-(cyclopropyl-methyl-amino)-4-ethyl-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-phenyl}-2-methyl-propionic acid methyl ester (Intermediate 182, 0.035 g, 0.076 mmol) in methanol (3 mL) and tetrahydrofuran (2 mL) was treated with 3M potassium hydroxide (2 mL, 4 mmol) and the resulting reaction mixture was heated at 80° C. for 2 days. The reaction mixture was neutralized with ammonium chloride and extracted with ethyl acetate. The organic phase was washed with water and brine, and dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford a residue that was purified by preparative reverse phase HPLC to afford the title product (0.023 g, 69%).

Workup

  1. customthe resulting reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford a residue that
  8. customwas purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-31375cef3b8345aaa33419ac7957d00e
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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