Tyramine → tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamate

HRID 974196Notes

Reaction equation

HRID 974196 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[C:11]([O:15][C:16](=O)[O:17]C(C)(C)C)([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C.C(O)(C)(C)C>O>[C:11]([O:15][C:16]([NH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 5610TyramineHCID 6386tert-ButanolHCID 8471TriethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 11831452tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamateYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 68.59 grams (0.5 mol) of tyramine (β-hydroxyphenylethylamine), 109.13 grams (0.5 mol) of di-t-butylcarbonate, 27.83 grams (0.275 mol) of triethylamine and 2700 ml of 80:20 t-butanol:deionized water solution was stirred for 16 hours at room temperature. The volume of the reaction mixture was reduced to 500-600 ml using a rotary evaporator. The viscous solution was extracted three times with 500 ml portions of chloroform. The chloroform extractions were combined, dried with anhydrous sodium sulfate, filtered and the chloroform was removed under reduced pressure. The product crystallized slowly to form a waxy solid and was recrystallized from acetonitrile. Based on method of preparation, there was obtained 116.13 grams (98% yield) of N-t-butoxycarbonyl tyramine (N-BOC-tyramine). The identity of the chainstopper was further confirmed by 1H NMR analysis.

Workup

  1. customa rotary evaporator
  2. extractionThe viscous solution was extracted three times with 500 ml portions of chloroform
  3. extractionThe chloroform extractions
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe chloroform was removed under reduced pressure
  7. customThe product crystallized slowly
  8. customto form a waxy solid
  9. customwas recrystallized from acetonitrile
  10. customBased on method of preparation

Sources & evidence

ORD record
ord-5d9fae28ce5a47a4b2a04232a71f7dd0
Source dataset
uspto-grants-1991_11
Patent number
US05068284

Reaction notes

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