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

HRID 582448Notes

Reaction equation

HRID 582448 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. NMR (DMSO-d6) among others: 7.36 (s,5H), 5.12 (dxd,2H), 3.989 (m,1H), 2.15 (t,2H), 1.38 (s,9H).

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-fe202ba6fc0b4ac895b15fe94d0f83b3
Source dataset
uspto-grants-1999_07
Patent number
US05925339

Reaction notes

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