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Ethyl(methoxy)amine hydrochloride → 2-tert-Butyl-6-chloro-benzooxazole-7-sulfonic acid ethyl-methoxy-amide

HRID 1669614
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HRID 1669614 반응식
Cl.[CH2:2]([NH:4][O:5][CH3:6])[CH3:3].[C:7]([C:11]1[O:12][C:13]2[C:19]([S:20](Cl)(=[O:22])=[O:21])=[C:18]([Cl:24])[CH:17]=[CH:16][C:14]=2[N:15]=1)([CH3:10])([CH3:9])[CH3:8]>C1COCC1.CCOC(C)=O>[CH2:2]([N:4]([O:5][CH3:6])[S:20]([C:19]1[C:13]2[O:12][C:11]([C:7]([CH3:9])([CH3:8])[CH3:10])=[N:15][C:14]=2[CH:16]=[CH:17][C:18]=1[Cl:24])(=[O:21])=[O:22])[CH3:3]
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참가 물질

5

반응물 2

HCID 22613948Ethyl(methoxy)amine hydrochloride2회HCID 234477912-Tert-butyl-6-chlorobenzoxazole-7-sulfonyl chloride

생성물 1

HCID 866386352-tert-Butyl-6-chloro-benzooxazole-7-sulfonic acid ethyl-methoxy-amide

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

N-Ethyl-O-methylhydroxylamine hydrochloride (Intermediate G) (3.39 g, 30.4 mmol) was suspended in dry THF (20 ml) and cooled to 0° C. in an ice bath while stirring. TEA (4.24 ml, 30.4 mmol) was added followed by dropwise addition of 2-tert-butyl-6-chloro-benzooxazole-7-sulfonyl chloride (US 2007/0249672 page 9) (4.68 g, 15.19 mmol) in THF (10 ml) over 2.5 hours. The reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with EtOAc and washed with H2O, brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography, eluting with 0-10% EtOAc in iso-hexane, to yield a white solid [M+H]+ 347.2

후처리

  1. stirringThe reaction mixture was stirred at room temperature for 30 minutes
  2. washwashed with H2O, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography
  6. washeluting with 0-10% EtOAc in iso-hexane
  7. customto yield a white solid [M+H]+ 347.2

출처 및 근거

ORD 기록
ord-209cf9fac31143a1b7a8edec201118e4
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07989497B2

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