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

HRID 2377413
Notes
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Reaction equation

HRID 2377413 reaction equation
C[O:2][C:3](=[O:26])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:21]([CH:23]3[CH2:25][CH2:24]3)[CH3:22])[CH:15]=2)=[CH:8][CH:7]=1.[OH-].[K+].Cl>CO.O1CCCC1>[CH:23]1([N:21]([CH2:20][C:16]2[CH:15]=[C:14]([C:13]#[C:12][C:9]3[CH:10]=[CH:11][C:6](/[CH:5]=[CH:4]/[C:3]([OH:26])=[O:2])=[CH:7][CH:8]=3)[CH:19]=[CH:18][CH:17]=2)[CH3:22])[CH2:24][CH2:25]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 57987781(E)-3-(4-{3-[(Cyclopropyl-methyl-amino)-methyl]-phenylethynyl}phenyl)-acrylic acid methyl ester2×

Product 1

HCID 11267548(E)-3-(4-{3-[(Cyclopropyl-methyl-amino)-methyl]-phenylethynyl}-phenyl)-acrylic acidYield 36%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (E)-3-(4-{3-[(cyclopropyl-methyl-amino)-methyl]-phenylethynyl}-phenyl)-acrylic acid methyl ester (Intermediate 92, 0.11 g, 0.32 mmol) in methanol (3 mL) and tetrahydrofuran (2 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 2 days. 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 10% methanol in ethyl acetate as the eluent to afford the title product as a yellow solid (0.038 g, 36%).

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-47a101dbfa88497fa82037aaf466baf4
Source dataset
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07468391B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes