Water → Ethyl [4-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-2'-methanesulfonyl-biphenyl-3-yloxy]acetate

HRID 733361ノート

反応式

HRID 733361 の反応式
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:32][CH3:33])=[C:7]([S:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S:27]([CH3:30])(=[O:29])=[O:28])=[CH:17][C:16]=2[OH:31])(=[O:11])=[O:10])[CH:8]=1)#[N:2].C(N(CC)C(C)C)(C)C.Br[CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46].O>CN(C)C=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:32][CH3:33])=[C:7]([S:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S:27]([CH3:30])(=[O:28])=[O:29])=[CH:17][C:16]=2[O:31][CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])(=[O:10])=[O:11])[CH:8]=1)#[N:2]

参加物

6

反応物 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 178562275-cyano-N-[2-(3-hydroxy-2'-methanesulfonylbiphenyl-4-yl)ethyl]-2-methoxybenzenesulfonamide

生成物 1

HCID 10393283Ethyl [4-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-2'-methanesulfonyl-biphenyl-3-yloxy]acetate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a solution of 5.72 g of 5-cyano-N-[2-(3-hydroxy-2′-methanesulfonylbiphenyl-4-yl)ethyl]-2-methoxybenzenesulfonamide in 57 mL of N,N-dimethylformamide were added 2.46 mL of N,N-diisopropylethylamine and 1.37 mL of ethyl bromoacetate. After being stirred at 50° C. for 15 hours, and the reaction mixture was poured into 100 mL of water, and extracted with a mixture of 150 mL of ethyl acetate and 20 mL of toluene. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on aminopropylated silica gel (eluent: ethyl acetate-hexane) to give 2.96 g of ethyl [4-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-2′-methanesulfonylbiphenyl-3-yloxy]acetate, amorphous.

後処理

  1. extractionextracted with a mixture of 150 mL of ethyl acetate and 20 mL of toluene
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by column chromatography on aminopropylated silica gel (eluent: ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-a1ff70530b5b4707b6fde6c010595bb5
出典データセット
uspto-grants-2009_09
特許番号
US07589126B2

反応ノート

読み込み中…