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Tetrahydrofuran → Di-tert-butyl ([(4-{2-[2-(acetylamino)-5-bromo-1,3-thiazol-4-yl]ethyl}phenyl)amino]methylidene}biscarbamate

HRID 1246461
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HRID 1246461 반응식
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][CH:19]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2].O1CCCC1.[Br:41]N1C(=O)CCC1=O>CO>[C:1]([NH:4][C:5]1[S:6][C:7]([Br:41])=[C:8]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([NH:18][CH:19]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:16][CH:17]=2)[N:9]=1)(=[O:3])[CH3:2]
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참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 67184N-bromobutanimideHCID 86595595Di-tert-butyl {[(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl)amino]methylidene}biscarbamate

생성물 1

HCID 86595594Di-tert-butyl ([(4-{2-[2-(acetylamino)-5-bromo-1,3-thiazol-4-yl]ethyl}phenyl)amino]methylidene}biscarbamate수율 75.7%

시약·촉매·용매 1

HCID 887
Methanol
용매

실험 절차

Di-tert-butyl {[(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl)amino]methylidene}biscarbamate (310 mg) prepared in a similar manner according to Step 5 of the following Production Example 18 was dissolved in methanol (6 ml) and tetrahydrofuran (3 ml) under nitrogen atmosphere. Then N-bromosuccinimide (164 mg) was added to the solution at 0° C. The reaction mixture was stirred at room temperature for 4 hours, and concentrated in vacuo. Chloroform and saturated sodium hydrogen carbonate solution were added to the residue. The organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography over silica gel with n-hexane/ethyl acetate (2:1) as an eluent to give di-tert-butyl {[(4-{2-[2-(acetylamino)-5-bromo-1,3-thiazol-4-yl]ethyl}phenyl)amino]methylidene}biscarbamate (271.4 mg) as a colorless amorphous substance.

후처리

  1. concentrationconcentrated in vacuo
  2. additionChloroform and saturated sodium hydrogen carbonate solution were added to the residue
  3. washThe organic layer was washed with water and saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography over silica gel with n-hexane/ethyl acetate (2:1) as an eluent

출처 및 근거

ORD 기록
ord-1380c10296ec477cb8a20c09e21261f8
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07125901B2

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