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HRID402208

反应详情

EQUATION

反应方程式

HRID 402208 的结构方程式

REACTANTS

反应物

1
结构：NCC[C@H](O)C(=O)N[C@@H]1C[C@H](N)[C@@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](N)[C@H]1O.O=S(=O)(O)O
HCID5458175

未命名化合物

PRODUCTS

生成物

1
结构：NCC[C@H](O)C(=O)N[C@@H]1C[C@H](N)[C@@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](N)[C@H]1O
HCID37768

Amikacin

C22H43N5O13

AUXILIARIES

试剂、催化剂与溶剂

1
结构：O
溶剂HCID962

Water

H2O

PROCEDURE

实验过程

Amikacin sulfate 1.0 grams (Commercially available from a number of chemical companies: O. M. Chemical Co., Ltd., Shanghai, China; Zhejiang Winsun Imp. & Exp. Co., Ltd, Zhejiang, China; Ningbo DHY Pharmaceutical Co., Zhejiang, China; and Shanghai Xudong Haipu Pharmaceutical Co., Ltd, Shanghai, China) was treated with 4 grams of Amberlite ion exchange resin (OH— form, Aldrich, Milwaukee, Wi) in 10 mL of water for 1 hour. The resultant solution was filtered and lyophilized to give Amikacin Free Base. The Amikacin free base (5.0 g, 8.5 mmoles) was dissolved in a mixture of 1,4-dioxane (165 mL) and H2O (235 mL). To this solution was added tert-butyloxycarbonyloxy-5-norbornene-2,3-dicarboxamide (1.3 g, 7.8 mmoles) dissolved in a mixture of CH2Cl2 (10 mL) and 1,4-dioxane (5 mL), over 50 min at room temperature. The reaction was stirred at room temp for 3 hours, and then evaporated under reduced pressure. The resultant solid was subjected to silica gel chromatography (4:4:2, MeOH, CH2Cl2, NH4OH, Rf=0.25) and then lyophilized to give the title compound, 1.6 g (30%) as a white solid.

WORKUP

后处理

  1. filtrationThe resultant solution was filtered