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

HRID 1040229
ノート
印刷プレビュー

反応式

HRID 1040229 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
110 °C

実験手順

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 (3 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

後処理

  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)

出典と根拠

ORDレコード
ord-41366ecbc2534b90a3ccfe4897a80b60
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08552196B2

反応ノート

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