Methyl iodide → HCID 15550576, compound

HRID 2268287Notes

Reaction equation

HRID 2268287 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[H-].[Na+].I[CH3:28]>CN(C)C=O.C(OCC)(=O)C>[C:21]([O:20][C:18](=[O:19])[CH2:17][CH2:16][N:15]([S:12]([C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:1][C:2]#[C:3][CH3:4])=[CH:11][CH:10]=1)(=[O:14])=[O:13])[CH3:28])([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15550574HCID 15550574, compound

Product 1

HCID 15550576HCID 15550576, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 3-({[4-(2-butynyloxy)phenyl]-sulfonyl}amino)propanoate (1.0 g, 2.83 mmol) in dimethylformamide (5 mL) at 0° C. was added sodium hydride (3.39 mmol) followed by iodomethane (211 uL, 3.39 mmol). After 72 hours the reaction mixture was diluted with ethyl acetate and washed with water and brine and dried over anhydrous sodium sulfate. Filtration and concentration in vacuo gave tert-butyl-3-[{[4-(2-butynyloxy)phenyl]-sulfonyl}(methyl)amino]propanoate (1.0 g) as a colorless oil. Electrospray Mass Spec 368.2 (M+H)+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-23e4d578954a40cd81b067b12c6d62bf
Source dataset
uspto-grants-2001_12
Patent number
US06326516B1

Reaction notes

Loading…