4-Nitrophenol → benzyloxycarbonyl-L-lysine amide

HRID 978335

Reaction equation

HRID 978335 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:18]([OH:20])=O)[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C([N+:27]([O-])=O)=CC=C(O)C=1.C1(N=C=NC2CCCCC2)CCCCC1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:18]([NH2:27])=[O:20])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 75172N-alpha-Benzyloxycarbonyl-L-lysineHCID 516892Sodium Bicarbonate

Product 1

HCID 7020264benzyloxycarbonyl-L-lysine amide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Na -t-butyloxycarbonyl-Ne -benzyloxycarbonyl-L-lysine was dissolved in ethyl acetate and esterified with p-nitrophenol using dicyclohexylcarbodiimide as a coupling agent. Sodium bicarbonate (10%) was added and the product extracted into the organic layer and crystallized from solution, then added to aqueous ammonium hydroxide to form Na -t-butyloxycarbonyl-Ne -benzyloxycarbonyl-L-lysine amide.

Workup

  1. extractionthe product extracted into the organic layer
  2. customcrystallized from solution
  3. additionadded to aqueous ammonium hydroxide

Sources & evidence

ORD record
ord-14bbdd6d54904e618df25400db7d786c
Source dataset
uspto-grants-1987_05
Patent number
US04665054

Linked notes

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