海萝胶 → N-acetyl-L-thyroxine N-(5-carboxypentyl)-carboxamide

HRID 1388088

反应方程式

HRID 1388088 反应方程式
[C:1]([NH:4][C@H:5]([C:25]([OH:27])=[O:26])[CH2:6][C:7]1[CH:14]=[C:12]([I:13])[C:11]([O:15][C:16]2[CH:23]=[C:21]([I:22])[C:20]([OH:24])=[C:18]([I:19])[CH:17]=2)=[C:9]([I:10])[CH:8]=1)(=[O:3])[CH3:2].O[N:29]1[C:33](=O)[CH2:32][CH2:31][C:30]1=[O:35].NCCC[CH2:40][CH2:41][C:42]([OH:44])=[O:43].C(=O)(O)[O-].[Na+].Cl>CN(C)C=O.O1CCCC1.O>[C:1]([NH:4][C@H:5]([C:25]([OH:27])=[O:26])[CH2:6][C:7]1[CH:14]=[C:12]([I:13])[C:11]([O:15][C:16]2[CH:17]=[C:18]([I:19])[C:20]([OH:24])=[C:21]([I:22])[CH:23]=2)=[C:9]([I:10])[CH:8]=1)(=[O:3])[CH3:2].[C:42]([CH2:41][CH2:40][CH2:31][CH2:32][CH2:33][NH:29][CH:30]=[O:35])([OH:44])=[O:43]

参与物

9

反应物 5

HCID 313海萝胶HCID 564氨基己酸HCID 80170N-羟基丁二酰亚胺HCID 516892碳酸氢钠HCID 20638380N-乙酰基L-甲状腺素

产物 1

HCID 131713378N-acetyl-L-thyroxine N-(5-carboxypentyl)-carboxamide收率 23%

试剂、催化剂与溶剂 3

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 6228N,N-二甲基甲酰胺溶剂HCID 8028四氢呋喃溶剂

实验过程

N-acetyl-L-thyroxine (Anal. Biochem., 33 (1970) 67) (1.0 g, 1.22 mmole) and N-hydroxysuccinimide (0.148 g, 1.28 mmole) are dissolved in 2 ml of dimethylformamide and 3 ml of tetrahydrofuran. Dicychlohexylcarbodiimide (0.264 g=1.28 mmole) is then added all at once and the reaction mixture stirred at room temperature for 4 hours. The dicyclohexylurea is removed by filtration and to the filtrate is added a solution of 6-aminocaproic acid (160 mg, 1.22 mmole) and sodium bicarbonate (204 mg, 2.44 mmole) in 1 ml of water. After stirring 2 hours the reaction mixture is acidified to pH 3 with 2 N HCl and extracted with methylene chloride. The organic extract is dried over magnesium sulfate and evaporated to the crude amide. Purification of the product is achieved by dissolving the crude material in methylene chloride containing a trace of methanol and precipitating the product with ether/hexane (75:25). The procedure is repeated two times to give 223 mg (23%) of pure product. It shows a single spot on TLC in 8% methanol in chloroform. The compound has the formula C22H24N2O6I4 and the following structure ##STR3##

后处理

  1. additionDicychlohexylcarbodiimide (0.264 g=1.28 mmole) is then added all at once and the reaction mixture
  2. customThe dicyclohexylurea is removed by filtration and to the filtrate
  3. stirringAfter stirring 2 hours the reaction mixture
  4. extractionextracted with methylene chloride
  5. extractionThe organic extract
  6. dry with materialis dried over magnesium sulfate
  7. customevaporated to the crude amide
  8. customPurification of the product
  9. dissolutionby dissolving the crude material in methylene chloride containing a trace of methanol
  10. customprecipitating the product with ether/hexane (75:25)

来源与证据

ORD记录
ord-27bbf48fdcab4675a0cf51d5e72fdb62
来源数据集
uspto-grants-1984_02
专利号
US04430263

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