Potassium Hydroxide → 3-(4-{3-[(Cyclopropyl-methyl-amino)-methyl]-phenylethynyl}-phenyl)-2-methyl-acrylic acid

HRID 1869936Notes

Reaction equation

HRID 1869936 reaction equation
C([O:3][C:4](=[O:28])[C:5]([CH3:27])=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][N:22]([CH:24]3[CH2:26][CH2:25]3)[CH3:23])[CH:16]=2)=[CH:9][CH:8]=1)C.[OH-].[K+]>C(O)C.O1CCCC1>[CH:24]1([N:22]([CH2:21][C:17]2[CH:16]=[C:15]([C:14]#[C:13][C:10]3[CH:11]=[CH:12][C:7]([CH:6]=[C:5]([CH3:27])[C:4]([OH:28])=[O:3])=[CH:8][CH:9]=3)[CH:20]=[CH:19][CH:18]=2)[CH3:23])[CH2:25][CH2:26]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 690699743-(4-{3-[(Cyclopropyl-methyl-amino)-methyl]-phenylethynyl}-phenyl)-2-methyl-acrylic acid ethyl ester2×

Product 1

HCID 690757123-(4-{3-[(Cyclopropyl-methyl-amino)-methyl]-phenylethynyl}-phenyl)-2-methyl-acrylic acidYield 83.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(4-{3-[(cyclopropyl-methyl-amino)-methyl]-phenylethynyl}-phenyl)-2-methyl-acrylic acid ethyl ester (Intermediate 94, 0.15 g, 0.4 mmol) in ethanol (3 mL) and tetrahydrofuran (3 mL) was treated with a 3M solution of potassium hydroxide (1 mL, 3 mmol) and the resulting reaction mixture was stirred at ambient temperature for overnight. The reaction mixture was concentrated, 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 to a solid. The solid was subjected to flash column chromatography using 5% methanol in ethyl acetate as the eluent to afford the title product as an amorphous solid (0.115 g, 83%).

Workup

  1. customthe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated to a solid

Sources & evidence

ORD record
ord-60dcdf47e05e4b408c22aba8ec38f31f
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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