Water → HCID 54155326, compound

HRID 620080Notes

Reaction equation

HRID 620080 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Br:24][CH2:25][CH2:26]Br.O>C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:26][CH2:25][Br:24])=[CH:15][CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 11831452tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamate

Product 1

HCID 54155326HCID 54155326, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 8.6 g (39 mmol) of crude N-tertiary butoxycarbonyltyramine, 27.6 g (200 mmol) of potassium carbonate and 73.3 g (390 mmol) of 1,2-dibromoethane is heated at boiling for 4 hours while stirring. The reaction mixture is cooled, and then 200 ml of water and 400 ml of ethyl acetate are added and the organic phase is separated off. After concentration by evaporation under reduced pressure, a crystalline residue remains which, after recrystallisation from 2-propanol, yields N-tertiary butoxycarbonyl-2-[p-(2-bromoethoxy)-phenyl]-ethylamine, which has a melting point of 70°-72°.

Workup

  1. temperatureis heated
  2. temperatureThe reaction mixture is cooled
  3. customthe organic phase is separated off
  4. concentrationAfter concentration
  5. customby evaporation under reduced pressure
  6. customafter recrystallisation from 2-propanol

Sources & evidence

ORD record
ord-b5d900708a814617b1c5ff058be697a7
Source dataset
uspto-grants-1989_04
Patent number
US04818766

Reaction notes

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