Triethylamine → ethyl 3-(1H-benzotriazol-1-yl)-2-cyclohexyl-3-oxopropanoate

HRID 1678615Notes

Reaction equation

HRID 1678615 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.CCN(CC)CC.[CH2:17]([O:19][C:20](=[O:31])[CH:21]([C:28](Cl)=[O:29])[CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH3:18]>C(Cl)Cl>[CH2:17]([O:19][C:20](=[O:31])[CH:21]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[C:28]([N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1)=[O:29])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 86640284Chlorocarbonyl-cyclohexyl-acetic acid ethyl esterHCID 178418385HCID 178418385, compound

Product 1

HCID 3722282ethyl 3-(1H-benzotriazol-1-yl)-2-cyclohexyl-3-oxopropanoateYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-cyclohexyl-malonic acid monoethyl ester (2.9 g, 14 mmol; CAS Reg. No. 147596-63-2) in thionyl chloride (29 ml) was heated under reflux conditions for 2 h. The solvent was removed under reduced pressure to give chlorocarbonyl-cyclohexyl-acetic acid ethyl ester. 1,2,3-Benzotriazole (1.47 g, 12 mmol) was dissolved at ambient temperature under an argon atmosphere in CH2Cl2 (45 ml). Et3N (1.86 ml, 13 mmol) and a solution of chlorocarbonyl-cyclohexyl-acetic acid ethyl ester in CH2Cl2 (4 ml) was added. The reaction mixture was stirred at ambient temperature for 14 h, quenched with ice cold aqueous 2 N HCl and extracted two times with iPrOAc. The combined extracts were washed with ice water/1 N aqueous HCl solution, ice water/brine 1/1 and dried over Na2SO4. After filtration the solvent was removed under reduced pressure to give a yellow oil which was purified by column chromatography (silica gel, iPrOAc/heptane) to give the title compound (1.05 g, 3.3 mmol; 25%) as yellow oil. MS: m/e=316.2 [M+H+].

Workup

  1. customquenched with ice cold aqueous 2 N HCl
  2. extractionextracted two times with iPrOAc
  3. washThe combined extracts were washed with ice water/1 N aqueous HCl solution, ice water/brine 1/1
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration the solvent
  6. customwas removed under reduced pressure
  7. customto give a yellow oil which
  8. customwas purified by column chromatography (silica gel, iPrOAc/heptane)

Sources & evidence

ORD record
ord-6e078718c98c4298871b391c482b9b32
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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