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HRID1071007

反应详情

EQUATION

反应方程式

HRID 1071007 的结构方程式

REACTANTS

反应物

4
结构：BrCc1ccccc1
HCID7498

alpha-Bromotoluene

C7H7Br

结构：O=C([O-])[O-].[K+].[K+]
HCID11430

Potassium Carbonate

CK2O3

结构：N[C@@H](Cc1ccc2ccccc2c1)C(=O)O
HCID185915

3-Naphthalen-2-ylalanine

C13H13NO2

结构：COc1ccnc(C(=O)N[C@H]2COC(=O)[C@H](Cc3ccccc3)[C@@H](O)[C@H](C)OC2=O)c1O
HCID11236123

未命名化合物

PRODUCTS

生成物

1
结构：COc1ccnc(C(=O)N[C@H]2COC(=O)[C@H](Cc3ccccc3)[C@@H](OC(=O)C(C)C)[C@H](C)OC2=O)c1OCc1ccccc1
HCID10282284

未命名化合物

收率 39%

AUXILIARIES

试剂、催化剂与溶剂

2
结构：CC(C)=O
溶剂HCID180

Acetone

C3H6O

结构：CCOC(C)=O
溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

Benzyl bromide (23.5 mL) was added to a solution of Nal (11.3 mol, 1.68 g) in acetone (60 mL). Compound 1 (22.5 mmol, 10 g) was added followed by powdered K2CO3.(38.8 mol, 5.3 g) and the mixture stirred vigorously overnight. The mixture was diluted with EtOAc (150 mL) and washed with H2O (2×150 mL). The organic layer was dried (MgSO4), and concentrated in vacuo. Purification via column chromatography (acetone/hexanes) gave 4.70 g (39%) of Compound 2 as an off-white solid. 1H-NMR and MS (M+1)+=535 were consistent for Compound 2.

WORKUP

后处理

  1. washwashed with H2O (2×150 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customPurification via column chromatography (acetone/hexanes)