Potassium Iodide → 2-(4-Benzyloxy-benzoyl)-4-cyclohexyl-butyric acid ethyl ester

HRID 270973Notes

Reaction equation

HRID 270973 reaction equation
[K].[CH2:2]([O:4][C:5](=[O:23])[CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)=[O:8])[CH3:3].[CH:24]1([CH2:30][CH2:31]Br)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.[I-].[K+]>CN(C)C=O>[CH2:2]([O:4][C:5](=[O:23])[CH:6]([C:7](=[O:8])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)[CH2:31][CH2:30][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[CH3:3]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 15440(2-Bromoethyl)cyclohexaneHCID 691555193-(4-Benzyloxy-phenyl)-3-oxo-propionic acid ethyl ester potassium salt

Product 1

HCID 588250192-(4-Benzyloxy-benzoyl)-4-cyclohexyl-butyric acid ethyl esterYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture 100 mg (0.3 mmol) of 3-(4-benzyloxy-phenyl)-3-oxo-propionic acid ethyl ester potassium salt, 86 mg (0.45 mmol) of 2-cyclohexylethyl bromide, and 17 mg (0.1 mmol) of potassium iodide (KI) in 1 mL of dimethylformamide (DMF) in a 4 mL vial was shaken in a sand bath at 80° C. overnight. The mixture was then concentrated to give a residue which was purified via reverse-phase chromatography (Gilson) to afford (after lyophilization) 85 mg (70% yield) of 2-(4-benzyloxy-benzoyl)-4-cyclohexyl-butyric acid ethyl ester as a solid as indicated by LC-MS—calcd for C26H32O2 [M++H]+: 409.23, found: 409.2.

Workup

  1. concentrationThe mixture was then concentrated
  2. customto give a residue which
  3. customwas purified via reverse-phase chromatography (Gilson)

Sources & evidence

ORD record
ord-6ffe2dce412744e6a66b370464e37b4a
Source dataset
uspto-grants-2008_11
Patent number
US07449488B2

Reaction notes

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