Acetyl chloride → HCID 86722312, compound

HRID 874821Notes

Reaction equation

HRID 874821 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].C(N(C(C)C)CC)(C)C.[C:28](Cl)(=[O:30])[CH3:29]>>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][N:8]([CH2:9][CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[C:28](=[O:30])[CH3:29]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 86722311HCID 86722311, compound

Product 1

HCID 86722312HCID 86722312, compoundYield 65.2%

Procedure

To an ice-cooled solution of N-(2-(1,3-dioxolan-2-yl)ethyl)-2-((tert-butyldimethylsilyl)oxy)ethanamine (0.85 g, 3.09 mmol) and di-iso-propylethylamine (0.82 mL, 4.63 mmol) was added acetyl chloride (0.26 mL, 3.71 mmol). The reaction mixture was stirred with ice-cooling for 1 hour, then the coolant was removed and stirring continued at RT for 18 hours. The reaction mixture was washed with saturated aqueous sodium hydrogen carbonate and the organic phase poured through a hydrophobic frit. The solvent was evaporated at reduced pressure to afford the title compound (0.64 g, 65%).

Workup

  1. temperaturecooling for 1 hour
  2. customthe coolant was removed
  3. stirringstirring
  4. washThe reaction mixture was washed with saturated aqueous sodium hydrogen carbonate
  5. additionthe organic phase poured through a hydrophobic frit
  6. customThe solvent was evaporated at reduced pressure

Sources & evidence

ORD record
ord-787710981845471baf05038efdd6af29
Source dataset
uspto-grants-2015_03
Patent number
US08980913B2

Reaction notes

Loading…