Methyl iodide → tert-butyl 5-(N-methyl-2-nitrophenylsulfonamido)pentylcarbamate

HRID 1408314노트

반응식

HRID 1408314 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:12])=[O:11])([O-:3])=[O:2].[C:27](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O.O.C(OC(C)C)(C)C>[CH3:27][N:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])[S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11]

참가 물질

7

반응물 3

HCID 6328Methyl iodide2회HCID 11430Potassium Carbonate2회HCID 67226448Tert-butyl 5-(2-nitrophenylsulfonamido)pentylcarbamate

생성물 1

HCID 86652975tert-butyl 5-(N-methyl-2-nitrophenylsulfonamido)pentylcarbamate수율 93.7%

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 7914Diisopropyl Ether용매

실험 절차

To a mixture of tert-butyl 5-(2-nitrophenylsulfonamido)pentylcarbamate 30c (32.61 g, 84 mmoles) and potassium carbonate (13.96 g, 1.2 eq) in acetone (300 mL) was added methyl iodide (5.5 mL, 1.05 eq). After stirring at RT overnight, more methyl iodide (1 eq) and potassium carbonate (0.6 eq) was added and the RM was stirred at RT until completion. The RM was then diluted with water and extracted with DCM. The organic layer was separated, washed with brine, dried over magnesium sulfate, filtered and concentrated. Trituration in diisopropyl ether afforded 31.59 g (93% yield) of tert-butyl 5-(N-methyl-2-nitrophenylsulfonamido)pentylcarbamate 30d as a white solid; m/z 402 [M+H]+.

후처리

  1. stirringthe RM was stirred at RT until completion
  2. extractionextracted with DCM
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b84bb504491f492cad09e69c4887f437
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921355B2

반응 노트

불러오는 중…