Benzyl chloroformate → HCID 54288704, compound

HRID 275873Notes

Reaction equation

HRID 275873 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.[OH-].[Na+].[C:13](Cl)([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>C(OCC)(=O)C>[CH2:16]([O:15][C:13]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1)=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 669044-Aminophenethyl alcohol

Product 1

HCID 54288704HCID 54288704, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Aminophenethyl alcohol (3.5 g) was dissolved in ethyl acetate (60 ml), to which was added 1N sodium hydroxide (50 ml). To the mixture was added, while stirring at room temperature, carbobenzoxy chloride (4.5 g). The mixture was stirred for 30 minutes. The organic layer was then separated, washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off to leave 4-benzyloxycarbonylaminophenethyl alcohol (4.5 g) as a liver brown crystalline product (4.5 g),

Workup

  1. additionTo the mixture was added
  2. stirringThe mixture was stirred for 30 minutes
  3. customThe organic layer was then separated
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-5afe2a93cba6431e93da17597ef0f2e3
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

Loading…