Amikacin Sulfate Salt → Amikacin

HRID 388198

Reaction equation

HRID 388198 reaction equation
[CH2:1]1[C@@H:6]([NH:7][C:8]([C@@H:10]([OH:14])[CH2:11][CH2:12][NH2:13])=[O:9])[C@H:5]([O:15][C@H:16]2[O:21][C@H:20]([CH2:22][OH:23])[C@@H:19]([OH:24])[C@H:18]([NH2:25])[C@H:17]2[OH:26])[C@@H:4]([OH:27])[C@H:3]([O:28][C@H:29]2[O:34][C@H:33]([CH2:35][NH2:36])[C@@H:32]([OH:37])[C@H:31]([OH:38])[C@H:30]2[OH:39])[C@H:2]1[NH2:40].OS(O)(=O)=O>O>[CH2:1]1[C@@H:6]([NH:7][C:8]([C@@H:10]([OH:14])[CH2:11][CH2:12][NH2:13])=[O:9])[C@H:5]([O:15][C@H:16]2[O:21][C@H:20]([CH2:22][OH:23])[C@@H:19]([OH:24])[C@H:18]([NH2:25])[C@H:17]2[OH:26])[C@@H:4]([OH:27])[C@H:3]([O:28][C@H:29]2[O:34][C@H:33]([CH2:35][NH2:36])[C@@H:32]([OH:37])[C@H:31]([OH:38])[C@H:30]2[OH:39])[C@H:2]1[NH2:40]

Participants

3

Reactant 1

HCID 5458175Amikacin Sulfate Salt

Product 1

HCID 37768Amikacin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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, Wis.) 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

  1. filtrationThe resultant solution was filtered

Sources & evidence

ORD record
ord-b7ff72f6b48f46debd8dcb5898fdd60a
Source dataset
uspto-grants-2013_02
Patent number
US08377896B2

Linked notes

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