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Trifluoroacetic acid → benzyl 3-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)phenylcarbamate

HRID 389614
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인쇄 미리보기

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HRID 389614 반응식
[CH2:1]([O:8][C:9](=[O:22])[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2O[CH:19]=[N:20][N:21]=2)[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:23]1([NH2:26])[CH2:25][CH2:24]1.FC(F)(F)C(O)=O>C(O)CCC>[CH2:1]([O:8][C:9](=[O:22])[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[N:26]([CH:23]3[CH2:25][CH2:24]3)[CH:19]=[N:20][N:21]=2)[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 69828CyclopropylamineHCID 66851996Benzyl 3-(1,3,4-oxadiazol-2-yl)phenylcarbamate

생성물 1

HCID 66851731benzyl 3-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)phenylcarbamate수율 31%

시약·촉매·용매 1

HCID 2631-Butanol용매

반응 조건

온도
110 °C

실험 절차

A mixture of (3-[1,3,4]Oxadiazol-2-yl-phenyl)-carbamic acid benzyl ester (200 mg, 0.68 mmol), cyclopropylamine (0.5 mL, 7.2 mmol), trifluoroacetic acid (0.05 mL, 0.65 mmol) in anhydrous 1-butanol mL) was heated at 110° C. overnight in a sealed tube. The reaction mixture was cooled to room temperature and the solvent was removed. The residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution, and the aqueous phase was extracted with ethyl acetate. Solvent was removed after drying with sodium sulfate and purified by silica gel chromatography (rf=0.26 in 20:1 ethyl acetate/methanol) to obtain [3-(4-Cyclopropyl-4H-[1,2,4]triazol-3-yl)-phenyl]-carbamic acid benzyl ester as a white powder (70 mg, 31%). M+1=335.1

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solvent was removed
  3. customThe residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. customSolvent was removed
  6. dry with materialafter drying with sodium sulfate
  7. custompurified by silica gel chromatography (rf=0.26 in 20:1 ethyl acetate/methanol)

출처 및 근거

ORD 기록
ord-b2542bd4a4ad43978a2f40767f1a1656
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08378108B2

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