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HRID582448

反应详情

EQUATION

反应方程式

HRID 582448 的结构方程式

REACTANTS

反应物

3
结构：ClCc1ccccc1
HCID7503

Benzyl chloride

C7H7Cl

结构：CC(C)(C)OC(=O)N[C@@H](CCC(N)=O)C(=O)O
HCID83687

L-Glutamine, N2-[(1,1-dimethylethoxy)carbonyl]-

C10H18N2O5

结构：C1=C(C2=NNCCCCCCCC2)CCCCCCCCC1
HCID53630274

未命名化合物

PRODUCTS

生成物

1
结构：CC(C)(C)OC(=O)N[C@@H](CCC(N)=O)C(=O)OCc1ccccc1
HCID13091521

未命名化合物

收率 59.8%

AUXILIARIES

试剂、催化剂与溶剂

2
结构：BrCc1ccccc1
催化剂HCID7498

alpha-Bromotoluene

C7H7Br

结构：C1CCOC1
溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

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

后处理

  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