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

HRID 1765803Notes

Reaction equation

HRID 1765803 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-cc29643ddce94a9790d3ed678cd901c5
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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