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

HRID 1408314ノート

反応式

HRID 1408314 の反応式
[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]

参加物

7

反応物 3

HCID 6328Methyl iodide2 回HCID 11430Potassium Carbonate2 回HCID 67226448Tert-butyl 5-(2-nitrophenylsulfonamido)pentylcarbamate

生成物 1

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

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 7914Diisopropyl Ether溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-b84bb504491f492cad09e69c4887f437
出典データセット
uspto-grants-2014_12
特許番号
US08921355B2

反応ノート

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