Sodium hydride → tert-butyl (4-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butyl)carbamate

HRID 474278

반응식

HRID 474278 반응식
[H-].[Na+].[C:3]([O:7][C:8](=[O:15])[NH:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])([CH3:6])([CH3:5])[CH3:4].F[C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1[N:26]1[CH:30]=[N:29][C:28]([CH3:31])=[N:27]1>C1COCC1>[CH3:31][C:28]1[N:29]=[CH:30][N:26]([C:18]2[CH:17]=[CH:22][C:21]([N+:23]([O-:25])=[O:24])=[CH:20][C:19]=2[O:14][CH2:13][CH2:12][CH2:11][CH2:10][NH:9][C:8](=[O:15])[O:7][C:3]([CH3:6])([CH3:4])[CH3:5])[N:27]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 545141tert-Butyl N-(4-hydroxybutyl)carbamateHCID 575269631-(2-fluoro-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole

생성물 1

HCID 66666004tert-butyl (4-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butyl)carbamate수율 99.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
0 °C

실험 절차

Sodium hydride (0.405 g, 10.13 mmol) was suspended in THF (6 mL), and then tert-butyl-(4-hydroxybutyl)carbamate (1.278 g, 6.75 mmol) in THF (6.0 mL) was added. The reaction mixture was stirred at 0° C. for 10 min, followed by the addition of 1-(2-fluoro-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole (1.0 g, 4.50 mmol) in THF (10.0 mL). The mixture was stirred at 0° C. for 1 h and then stirred for an additional 2 h at rt. The reaction was quenched with water and extracted with EtOAc three times. After concentrating the combined EtOAc layers, the residue was purified by flash chromatography (silica gel, 300 g, 0 to 80% EtOAc/Hexane) to get tert-butyl (4-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butyl)carbamate (1.75 g, 99% yield). LC-MS (M+Na)+=414.5. 1H NMR (500 MHz, chloroform-d) δ 8.88 (s, 1H), 8.10 (d, J=8.8 Hz, 1H), 8.00 (dd, J=8.9, 2.3 Hz, 1H), 7.95 (d, J=2.3 Hz, 1H), 4.28 (t, J=6.5 Hz, 2H), 3.22 (d, J=6.4 Hz, 2H), 2.52 (s, 3H), 2.01-1.92 (m, 2H), 1.74-1.68 (m, 2H), 1.46 (s, 9H).

후처리

  1. stirringThe mixture was stirred at 0° C. for 1 h
  2. stirringstirred for an additional 2 h at rt
  3. customThe reaction was quenched with water
  4. extractionextracted with EtOAc three times
  5. concentrationAfter concentrating the combined EtOAc layers
  6. customthe residue was purified by flash chromatography (silica gel, 300 g, 0 to 80% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-6b08aa0f3d744230b084b5631f29c42d
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637523B2

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