Ethanol → (7e)-7-Hydroxyimino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-sulfonic acid[2-(4-fluorophenyl)-2-hydroxyethyl]-methyl-amide

HRID 1351325노트

반응식

HRID 1351325 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:25])[CH2:9][N:10]([CH3:24])[S:11]([C:14]2[C:15]3[CH2:22][CH2:21][CH2:20][C:19](=O)[C:16]=3[S:17][CH:18]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.C(O)C.Cl.[OH:30][NH2:31].C([O-])(=O)C.[Na+]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:25])[CH2:9][N:10]([CH3:24])[S:11]([C:14]2[C:15]3[CH2:22][CH2:21][CH2:20]/[C:19](=[N:31]/[OH:30])/[C:16]=3[S:17][CH:18]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 77617953HCID 77617953, 화합물

생성물 1

HCID 11350049(7e)-7-Hydroxyimino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-sulfonic acid[2-(4-fluorophenyl)-2-hydroxyethyl]-methyl-amide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 7-oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-3-sulfonic acid [2-(4-fluorophenyl)-2-hydroxyethyl]-methyl-amide (the compound of Preparation Example 48) (150 mg) in tetrahydrofuran (3 mL) and ethanol (3 mL) was added an aqueous solution (2.5 mL) of hydroxyamine hydrochloride (112 mg) and sodium acetate (133 mg), and the mixture was stirred at 70–80° C. for 3 hours. The organic solvent was removed by evaporation, water and ethyl acetate were added for separation/extraction. The organic layer was dried with anhydrous magnesium sulfate, the solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate; ethyl acetate 10–40%). Among the 2 spots detected by TLC (the solvent system; hexane-ethyl acetate=1:1), the polar fractions (low Rf value on TLC) were collected, and the title compound (116 mg) was obtained as a colorless solid.

후처리

  1. customThe organic solvent was removed by evaporation, water and ethyl acetate
  2. additionwere added for separation/extraction
  3. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate; ethyl acetate 10–40%)
  6. customhexane-ethyl acetate=1:1), the polar fractions (low Rf value on TLC) were collected

출처 및 근거

ORD 기록
ord-0aa6044052e74deeb88d5c78cac143f2
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07217723B2

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