Benzyl Chloride → Benzyl (tert-butoxycarbonyl)-L-glutaminate

HRID 1858390Notes

Reaction equation

HRID 1858390 reaction equation
[C:1]([NH:8][C@H:9]([C:15]([OH:17])=[O:16])[CH2:10][CH2:11][C:12](=[O:14])[NH2:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>O1CCCC1.C(Br)C1C=CC=CC=1>[CH2:18]([O:16][C:15](=[O:17])[C@H:9]([CH2:10][CH2:11][C:12](=[O:14])[NH2:13])[NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 83687L-Glutamine, N2-((1,1-dimethylethoxy)carbonyl)-HCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 13091521Benzyl (tert-butoxycarbonyl)-L-glutaminateYield 59.8%

Reagents, catalysts & solvents 2

HCID 7498Benzyl BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

147 g N-BOC-glutamin (t-butyloxycarbonyl-glutamin), 77 g benzylchloride and 4 g benzylbromide were refluxed in 600 ml tetrahydrofuran for 2.5 hours in the presence of a 5% excess of diazabicycloundecene. After the removal of the solvent, the residue was taken up in water-ethylacetate and washed with citric acid, sodium bicarbonate and water. Evaporating of the solvent and recrystallization from ethylacetate-hexane gave 120 g white crystals.

Workup

  1. customAfter the removal of the solvent
  2. washwashed with citric acid, sodium bicarbonate and water
  3. customEvaporating of the solvent and recrystallization from ethylacetate-hexane

Sources & evidence

ORD record
ord-575625c76da24224bf9b475dc380da41
Source dataset
uspto-grants-2000_11
Patent number
US06150542

Reaction notes

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