Water → (7R)-7-({[t-Butyl(dimethyl)silyl]oxy}methyl)-7-methyl-5-(methylthio)-2,3,6,7-tetrahydro-1,4-thiazepine

HRID 1423979Notes

Reaction equation

HRID 1423979 reaction equation
[Si:1]([O:8][CH2:9][C@:10]1([CH3:18])[S:16][CH2:15][CH2:14][NH:13][C:12](=[S:17])[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[K+].O.[CH3:22]I>O1CCCC1>[Si:1]([O:8][CH2:9][C@:10]1([CH3:18])[S:16][CH2:15][CH2:14][N:13]=[C:12]([S:17][CH3:22])[CH2:11]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 71466070(7R)-7-({[t-Butyl(dimethyl)silyl]oxy}methyl)-7-methyl-1,4-thiazepane-5-thione

Product 1

HCID 71466071(7R)-7-({[t-Butyl(dimethyl)silyl]oxy}methyl)-7-methyl-5-(methylthio)-2,3,6,7-tetrahydro-1,4-thiazepineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (2.00 g, 6.54 mmol) obtained in Example 4-0) was dissolved in tetrahydrofuran (11 mL). Potassium hydroxide (2.16 g, 39.72 mmol), water (7 mL), and methyl iodide (2.44 mL, 39.27 mmol) were added to the solution at room temperature, and the mixture was stirred for 1 h under a nitrogen atmosphere. The reaction mixture was extracted with ethyl acetate (50 mL), and the organic layer was washed with saturated sodium chloride solution and then dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (2.09 g, quant.) in a yellow oily form.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (50 mL)
  2. washthe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0c00cd22d108441d810bc3e110a25e32
Source dataset
uspto-grants-2015_01
Patent number
US08927536B2

Reaction notes

Loading…