Acetyl chloride → HCID 45091997, compound

HRID 1670024Notes

Reaction equation

HRID 1670024 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:12](Cl)(=[O:14])[CH3:13]>C(Cl)Cl>[C:1]([NH:8][CH2:9][CH2:10][O:11][C:12](=[O:14])[CH3:13])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 45091997HCID 45091997, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(BOC)aminoethanol (3.2 g, 20.0 mmol) in DCM (60 mL) were added TEA (5.6 mL, 40.0 mL) and acetyl chloride (3.36 mL, 30 mmol) at 0° C. After the reaction solution was stirred for 2 h, the solvent was removed, and the residue dissolved in water. The organic material was extracted with EtOAc, and the extracts were washed with 1N HCl, dried over MgSO4, concentrated in vacuo. The residue was purified by column chomatography (eluent: EtOAc/Hex=1/10) to give the title compound (3.2 g, 80%).

Workup

  1. customthe solvent was removed
  2. dissolutionthe residue dissolved in water
  3. extractionThe organic material was extracted with EtOAc
  4. washthe extracts were washed with 1N HCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chomatography (eluent: EtOAc/Hex=1/10)

Sources & evidence

ORD record
ord-119bb2e2f8c04b3ea36dcbc8c6e7241f
Source dataset
uspto-grants-2011_08
Patent number
US07989634B2

Reaction notes

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