Triethylamine → Ethyl[2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetate

HRID 1272418Notes

Reaction equation

HRID 1272418 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][C:5]=1[O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].C(N(CC)CC)C.[C:27]([C:29]1[CH:30]=[CH:31][C:32]([O:39][CH3:40])=[C:33]([S:35](Cl)(=[O:37])=[O:36])[CH:34]=1)#[N:28]>O1CCCC1.O>[C:27]([C:29]1[CH:30]=[CH:31][C:32]([O:39][CH3:40])=[C:33]([S:35]([NH:1][CH2:2][CH2:3][C:4]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:18])[CH3:19])=[CH:13][C:5]=2[O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:37])=[O:36])[CH:34]=1)#[N:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 115287515-Cyano-2-methoxybenzene-1-sulfonyl chlorideHCID 18456985Ethyl[2-(2-aminoethyl)-5-isopropylphenoxy]acetate

Product 1

HCID 17856206Ethyl[2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetateYield 72.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 326 mg of ethyl [2-(2-amino-ethyl)-5-isopropylphenoxy]acetate hydorochloride and 0.452 mL of triethylamine in a mixture of 10 mL of tetrahydrofuran and 5 mL of water was added 238 mg of 5-cyano-2-methoxybenzene-sulfonyl chloride under ice-cooling, and the mixture was stirred at room temperature for 6 hours. To the reaction mixture was added 30 mL of water, and the mixture was extracted with 120 mL of ethyl acetate. The organic layer was washed with 100 mL of water, and 100 mL of brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane) to give 343 mg of ethyl [2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetate.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with 120 mL of ethyl acetate
  3. washThe organic layer was washed with 100 mL of water, and 100 mL of brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-4b4a1d7814484c3abc098f95eb3415b7
Source dataset
uspto-grants-2007_04
Patent number
US07208524B2

Reaction notes

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