Hydrochloric Acid → Ethyl[4-[2-(5-cyano-2-hydroxybenzenesulfonylamino)ethyl]-2'-methanesulfonyl-biphenyl-3-yloxy]acetate

HRID 733369노트

반응식

HRID 733369 반응식
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:38]C)=[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[O:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])(=[O:11])=[O:10])[CH:8]=1)#[N:2].[Cl-].[Li+].C(OCC)(=O)C.Cl>CN(C)C=O.C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:38])=[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[O:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])(=[O:10])=[O:11])[CH:8]=1)#[N:2]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 433294Lithium ChlorideHCID 10393283Ethyl [4-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-2'-methanesulfonyl-biphenyl-3-yloxy]acetate

생성물 1

HCID 12149205Ethyl[4-[2-(5-cyano-2-hydroxybenzenesulfonylamino)ethyl]-2'-methanesulfonyl-biphenyl-3-yloxy]acetate수율 81.4%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6228Dimethylformamide용매

반응 조건

온도
140 °C

실험 절차

To a solution of 4.62 g of ethyl [4-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-2′-methanesulfonylbiphenyl-3-yloxy]acetate in 40 mL of N,N-dimethylformamide was added 1.03 g of lithium chloride, and the mixture was stirred at 140° C. for 2 hours. After being cooled to room temperature, the reaction mixture was poured into a mixture of 60 mL of ethyl acetate, 6 mL of toluene, and 32 mL of 1 mol/L hydrochloric acid. The organic layer was separated, and washed with 1 mol/L hydrochloric acid and brine. The organic layer was 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: acetic acid-ethyl acetate) to give 3.67 g of ethyl [4-[2-(5-cyano-2-hydroxybenzenesulfonylamino)ethyl]-2′-methanesulfonylbiphenyl-3-yloxy]acetate, colorless and amorphous.

후처리

  1. temperatureAfter being cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with 1 mol/L hydrochloric acid and brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by column chromatography on aminopropylated silica gel (eluent: acetic acid-ethyl acetate)

출처 및 근거

ORD 기록
ord-b0b7ec296bbe4503a5add63ea1fa48fe
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589126B2

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