Methyl iodide → HCID 66657855, compound

HRID 420608Notes

Reaction equation

HRID 420608 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[S:15][C:16]3[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:17]=3[N:18]=2)[C@H:10]([CH2:27][OH:28])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:29]I.[H-].[Na+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[S:15][C:16]3[CH:22]=[C:21]([C:23]([F:25])([F:24])[F:26])[CH:20]=[CH:19][C:17]=3[N:18]=2)[C@H:10]([CH2:27][O:28][CH3:29])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66658219HCID 66658219, compound

Product 1

HCID 66657855HCID 66657855, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-3-hydroxymethyl-4-(6-trifluoromethyl benzothiazole-2-yl) piperazine-1-carboxylic acid t-butyl ester (209 mg) in dimethylformamide (2 mL) were sequentially added methyl iodide (0.5 mL) and sodium hydride (62.4 mg). The mixture was stirred at room temperature for 24 hours. To the reaction solution was added ice water and extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph on silica gel to give the title compound (167 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulphate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record
ord-03f16fc0324a4de984166099c1ae28d3
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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