Hydrochloric Acid → (E)-3-(4-{5-[(Cyclopropyl-methyl-amino)-methyl]-2-methyl-phenylethynyl}-phenyl)-acrylic acid

HRID 1869943Notes

Reaction equation

HRID 1869943 reaction equation
C([O:3][C:4](=[O:28])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:20]=[C:19]([CH2:21][N:22]([CH:24]3[CH2:26][CH2:25]3)[CH3:23])[CH:18]=[CH:17][C:16]=2[CH3:27])=[CH:9][CH:8]=1)C.[OH-].[K+].Cl>C(O)C.O1CCCC1>[CH:24]1([N:22]([CH2:21][C:19]2[CH:18]=[CH:17][C:16]([CH3:27])=[C:15]([C:14]#[C:13][C:10]3[CH:9]=[CH:8][C:7](/[CH:6]=[CH:5]/[C:4]([OH:28])=[O:3])=[CH:12][CH:11]=3)[CH:20]=2)[CH3:23])[CH2:25][CH2:26]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 57462494(E)-3-(4-{5-[(Cyclopropyl-methyl-amino)-methyl]-2-methyl-phenylethynyl}-phenyl)-acrylic acid ethyl ester2×

Product 1

HCID 57462495(E)-3-(4-{5-[(Cyclopropyl-methyl-amino)-methyl]-2-methyl-phenylethynyl}-phenyl)-acrylic acidYield 55.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (E)-3-(4-{5-[(cyclopropyl-methyl-amino)-methyl]-2-methyl-phenylethynyl}-phenyl)-acrylic acid ethyl ester (Intermediate 100, 0.14 g, 0.37 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 overnight. The reaction mixture was neutralized with 5% aqueous hydrochloric acid 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 a residue that was subjected to flash column chromatography over silica gel (230-400 mesh) using 5% methanol in ethyl acetate as the eluent to afford the title product as an amorphous solid (0.071 g, 55%).

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 to a residue that

Sources & evidence

ORD record
ord-ffe4a2cb7f534ebf9d978d83f95aea40
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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