1,8-Diazabicyclo(5.4.0)undec-7-ene → N6-[[(4-Azidophenyl)methoxy]carbonyl]-L-lysine

HRID 1482333Notes

Reaction equation

HRID 1482333 reaction equation
C1CCN2C(=NCCC2)CC1.C1C2C(COC([NH:29][C@@H:30]([CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][CH2:42][C:43]3[CH:48]=[CH:47][C:46]([N:49]=[N+:50]=[N-:51])=[CH:45][CH:44]=3)=[O:40])[C:31]([OH:33])=[O:32])=O)C3C(=CC=CC=3)C=2C=CC=1>CN(C=O)C>[NH2:29][C@@H:30]([CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][CH2:42][C:43]1[CH:44]=[CH:45][C:46]([N:49]=[N+:50]=[N-:51])=[CH:47][CH:48]=1)=[O:40])[C:31]([OH:33])=[O:32]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 89668615HCID 89668615, compound

Product 1

HCID 89668613N6-[[(4-Azidophenyl)methoxy]carbonyl]-L-lysineYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DBU (0.064 mL, 0.425 mmol) was added to a solution of (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-((((4-azidobenzyl)oxy)carbonyl)amino)hexanoic acid (Compound SP661) (210 mg, 0.386 mmol) in DMF (0.7 mL) at room temperature under a nitrogen atmosphere. The resulting reaction mixture was stirred at the same temperature for 20 minutes and then purified by reverse-phase silica gel column chromatography (0.05% aqueous trifluoroacetic acid solution/0.05% trifluoroacetic acid-acetonitrile solution) to afford (S)-2-amino-6-((((4-azidobenzyl)oxy)carbonyl)amino)hexanoic acid (Lys(Acbz)) (Compound tk34) (100 mg, 81%).

Workup

  1. customThe resulting reaction mixture
  2. custompurified by reverse-phase silica gel column chromatography (0.05% aqueous trifluoroacetic acid solution/0.05% trifluoroacetic acid-acetonitrile solution)

Sources & evidence

ORD record
ord-4071b0de7f5d442fb1e9e609e9cc3ae5
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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