Cyclohexaneacetic acid → HCID 59714994, compound

HRID 2223851Notes

Reaction equation

HRID 2223851 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][OH:11].[CH:12]1([CH2:18][C:19](O)=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>ClCCl.C(Cl)(Cl)Cl>[CH:12]1([CH2:18][C:19]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][CH2:9][CH2:10][OH:11])=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 21363Cyclohexaneacetic acidHCID 757711-HydroxybenzotriazoleHCID 2204233-(2-aminophenyl)propan-1-olHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 59714994HCID 59714994, compoundYield 51.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2-aminophenyl)propan-1-ol (180 mg) and cyclohexylacetic acid (203 mg) in dichioromethane (12mL) were added 1-hydroxybenzotriazole (193 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (274 mg) under ice cooling. The solution was stirred at room temperature for 113 hours. Chloroform was then added to the solution and it was washed in turn with water and saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography (silica gel, hexane: ethyl acetate=1:1) to give the title compound (170 mg).

Workup

  1. washwas washed in turn with water and saturated aqueous sodium bicarbonate solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by column chromatography (silica gel, hexane: ethyl acetate=1:1)

Sources & evidence

ORD record
ord-0ad59ea42a984edf8c416c3cb2448518
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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