Methyl iodide → HCID 86654679, compound

HRID 1807643Notes

Reaction equation

HRID 1807643 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][CH2:22][CH2:23][CH2:24][CH3:25])(=[O:12])=[O:11])([O-:3])=[O:2].[C:27](=O)([O-])[O-].[K+].[K+].CI.ClCCl>CC(C)=O.O>[CH3:27][N:13]([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])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 86654680HCID 86654680, compound

Product 1

HCID 86654679HCID 86654679, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of tent-butyl (5-{[(2-nitrophenyl)sulfonyl]amino}pentyl)carbamate 55 (32.6 g, 84 mmol) in acetone (300 mL) was added potassium carbonate (23.2 g, 168 mmol). The resulting mixture was stirred at room temperature for 30 minutes then methyl iodide (17.88 g, 126 mmol) was added drop wise. The resulting mixture was stirred at room temperature overnight. The reaction mixture was poured in water and dichloromethane was added. The organic layer was separated and successively dried over MgSO4 filtered and concentrated. The residue was triturated with di-isopropyl ether to yield 31.6 g 93% of tent-butyl (5-{methyl[(2-nitrophenyl)sulfonyl]amino}pentyl)carbamate 56 as a white powder m/z 402 [M+H]+.

Workup

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. customThe organic layer was separated
  3. dry with materialsuccessively dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was triturated with di-isopropyl ether

Sources & evidence

ORD record
ord-c2da4153cf7f4d648df7da630a52db11
Source dataset
uspto-grants-2013_01
Patent number
US08357687B2

Reaction notes

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