Hydrochloric Acid → N-acetyl-L-thyroxine N-(5-carboxypentyl)-carboxamide

HRID 1388088

Reaktionsgleichung

Reaktionsgleichung von HRID 1388088
[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]

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 5646-Aminohexanoic AcidHCID 80170N-HydroxysuccinimideHCID 516892Sodium BicarbonateHCID 20638380N-Acetylthyroxine

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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##

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-27bbf48fdcab4675a0cf51d5e72fdb62
Quelldatensatz
uspto-grants-1984_02
Patentnummer
US04430263

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