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3-Butyn-1-OL → 2-Chloro-N-(1-hydroxy-cycloheptylmethyl)-5-[5-(2-hydroxy-ethyl)-isoxazol-3-yl]-benzamide

HRID 456890
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HRID 456890 반응식
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([CH:20]=[N:21][OH:22])=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:5].[CH2:23]([OH:27])[CH2:24][C:25]#[CH:26].Cl[O-].[Na+]>C(N(CC)CC)C.ClCCl.O>[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]2[CH:26]=[C:25]([CH2:24][CH2:23][OH:27])[O:22][N:21]=2)=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1)=[O:5]
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참가 물질

7

반응물 3

HCID 135663-Butyn-1-OLHCID 23665760Sodium HypochloriteHCID 724346312-Chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(hydroxyimino-methyl)-benzamide

생성물 1

HCID 588181972-Chloro-N-(1-hydroxy-cycloheptylmethyl)-5-[5-(2-hydroxy-ethyl)-isoxazol-3-yl]-benzamide수율 22.1%

시약·촉매·용매 3

HCID 8471Triethylamine촉매
HCID 962
Water
용매
HCID 6344Dichloromethane용매

실험 절차

A mixture of 2-chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(hydroxyimino-methyl)-benzamide (50 mg, 0.15 mmol), but-3-yn-1-ol (27 mg, 0.38 mmol), sodium hypochlorite (1 mL, 4%) and triethylamine (2 drops) in dichloromethane (2 mL) was stirred at room temperature for 5 d. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water, and brine, dried over sodium sulfate, filtered and adsorbed onto silica gel. The residue was purified by flash column chromatography (65% ethyl acetate-hexanes) to afford the title compound (13 mg).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with water, and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customThe residue was purified by flash column chromatography (65% ethyl acetate-hexanes)

출처 및 근거

ORD 기록
ord-2c97d1b225fe4cfaab4450f4f3046fa1
출처 데이터셋
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07186742B2

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