Potassium Hydroxide → HCID 69077442, compound

HRID 1869934Notes

Reaction equation

HRID 1869934 reaction equation
C([O:3][C:4](=[O:28])[CH:5]=[C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][N:23]([CH:25]3[CH2:27][CH2:26]3)[CH3:24])[CH:17]=2)=[CH:10][CH:9]=1)[CH3:7])C.[OH-].[K+]>C(O)C.O1CCCC1>[CH:25]1([N:23]([CH2:22][C:18]2[CH:17]=[C:16]([C:15]#[C:14][C:11]3[CH:12]=[CH:13][C:8]([C:6]([CH3:7])=[CH:5][C:4]([OH:28])=[O:3])=[CH:9][CH:10]=3)[CH:21]=[CH:20][CH:19]=2)[CH3:24])[CH2:26][CH2:27]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 69074665HCID 69074665, compound2×

Product 1

HCID 69077442HCID 69077442, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(4-{3-[(cyclopropyl-methyl-amino)-methyl]-phenylethynyl}-phenyl)-but-2-enoic acid ethyl ester (Intermediate 93, 0.17 g, 0.46 mmol) in ethanol (3 mL) and tetrahydrofuran (3 mL) was treated with a 3.4M solution of potassium hydroxide (1 mL, 3.4 mmol) and the resulting reaction mixture was stirred at ambient temperature for 36 h. The reaction mixture was extracted with diethyl ether, and the aqueous phase was neutralized with 10% aqueous hydrochloric acid and evaporated to a solid. The solid was subjected to flash column chromatography using ethyl acetate as the eluent to afford the title product as a white solid (0.05 g, 32%). 1H NMR (300 MHz, CDCl3): δ 7.49-7.43 (m, 4H), 7.32-7.20 (m, 4H), 5.93 (s, 1H), 3.70 (s, 2H), 2.29 (s, 3H), 2.17 (s, 3H), 1.76-1.73 (m, 1H), 0.50-0.48 (m, 4H).

Workup

  1. customthe resulting reaction mixture
  2. extractionThe reaction mixture was extracted with diethyl ether
  3. customevaporated to a solid

Sources & evidence

ORD record
ord-8853df203a4d49c793f5500049d1e30e
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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