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

HRID 1486419Notes

Reaction equation

HRID 1486419 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 7914Diisopropyl EtherSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-a8aff868c05348d098e8a376cf009d53
Source dataset
uspto-grants-2016_08
Patent number
US09427440B2

Reaction notes

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