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Ethanol → N-hydroxy-2-[[4-methoxybenzenesulfonyl](benzyl)amino]-2-[(2-methyl-5-tetrazolyl)methyl]acetamide

HRID 742057
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인쇄 미리보기

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HRID 742057 반응식
C([O:5][NH:6][C:7](=[O:35])[CH:8]([N:16]([S:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)(=[O:26])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:9][C:10]1[N:11]=[N:12][N:13]([CH3:15])[N:14]=1)(C)(C)C.C(O)C>C(Cl)Cl>[OH:5][NH:6][C:7](=[O:35])[CH:8]([N:16]([S:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)(=[O:26])=[O:25])[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:9][C:10]1[N:11]=[N:12][N:13]([CH3:15])[N:14]=1
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참가 물질

4

반응물 2

HCID 702EthanolHCID 22907048N-(t-butyloxy)-2-[[4-methoxybenzenesulfonyl](benzyl)amino]-2-[(2-methyl-5-tetrazolyl)methyl]acetamide

생성물 1

HCID 22907172N-hydroxy-2-[[4-methoxybenzenesulfonyl](benzyl)amino]-2-[(2-methyl-5-tetrazolyl)methyl]acetamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

N-(t-butyloxy)-2-[[4-methoxybenzenesulfonyl](benzyl)amino]-2-[(2-methyl-5-tetrazolyl)methyl]acetamide (0.77 g, 1.55 mmol) is dissolved in methylene chloride (2.0 mL) and ethanol (0.1 mL) in a glass sealed tube, and the reaction is cooled to 0° C. Hydrochloric acid gas (from a lecture bottle) is bubbled through the solution for 20 minutes, and then the tube is sealed at room temperature for 3 days. After that time, the solvent is removed, and the reaction is partitioned between ethyl acetate and saturated sodium bicarbonate. The organic phase is dried (Na2SO4), and the solvent is evaporated. The product is purified by silica gel chromatography (2% methanol/methylene chloride) to give N-hydroxy-2-[[4-methoxybenzenesulfonyl](benzyl)amino]-2-[(2-methyl-5-tetrazolyl)methyl]acetamide, m.p. 72°-75° C.

후처리

  1. customHydrochloric acid gas (from a lecture bottle) is bubbled through the solution for 20 minutes
  2. customthe tube is sealed at room temperature for 3 days
  3. customAfter that time, the solvent is removed
  4. customthe reaction is partitioned between ethyl acetate and saturated sodium bicarbonate
  5. dry with materialThe organic phase is dried (Na2SO4)
  6. customthe solvent is evaporated
  7. customThe product is purified by silica gel chromatography (2% methanol/methylene chloride)

출처 및 근거

ORD 기록
ord-9d5970b1cdd84e569771486c20fd7e57
출처 데이터셋
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05552419

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