Triethylamine → 1-Cyclohexylmethyl-2-oxo-1,2,5,6,7,8,9,10-octahydro-cycloocta[b]pyridine-3-carboxylic acid (2-oxo-tetrahydrofuran-3-yl)-amide

HRID 383547

Reaktionsgleichung

Reaktionsgleichung von HRID 383547
[CH:1]1([CH2:7][N:8]2[C:13](=[O:14])[C:12]([C:15](O)=[O:16])=[CH:11][C:10]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:9]2=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br.[NH2:25][CH:26]1[CH2:30][CH2:29][O:28][C:27]1=[O:31].C(N(CC)CC)C.CCCCCC.C(OCC)(=O)C>C1COCC1>[O:31]=[C:27]1[CH:26]([NH:25][C:15]([C:12]2[C:13](=[O:14])[N:8]([CH2:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[C:9]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:10]=3[CH:11]=2)=[O:16])[CH2:30][CH2:29][O:28]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 73508Homoserine lactone hydrobromideHCID 21226206Ethyl acetate hexaneHCID 597188051-Cyclohexylmethyl-2-oxo-1,2,5,6,7,8,9,10-octahydro-cycloocta[b]pyridine-3-carboxylic acid

Produkt 1

HCID 597188781-Cyclohexylmethyl-2-oxo-1,2,5,6,7,8,9,10-octahydro-cycloocta[b]pyridine-3-carboxylic acid (2-oxo-tetrahydrofuran-3-yl)-amideAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1-Cyclohexylmethyl-2-oxo-1,2,5,6,7,8,9,10-octahydro-cycloocta[b]pyridine-3-carboxylic acid (AA01, 250 mg, 0.788 mmol) which had been obtained in Example 1 was made to be the acid chloride according to the conventional method, and the acid chloride was dissolved in THF. Then, the solution was dropped into the DMF (2 mL) mixed liquid of 3-amino-dihydro-furan-2-one hydrobromide (187 mg, 1.03 mmol) and triethylamine (0.38 mL, 2.36 mmol) while cooling with ice. After that, the mixture was stirred at the same temperature for 30 minutes, and further stirred continuously at room temperature for 3 hours. The mixture was subjected to the same after-treatment as described above, and then refined with silica gel column chromatography (hexane-ethyl acetate (40 to 60%)), and I-072 was obtained as a colorless solid (242 mg, 77%, mp: 136-140° C.).

Aufarbeitung

  1. temperaturewhile cooling with ice
  2. stirringfurther stirred continuously at room temperature for 3 hours

Quellen und Nachweise

ORD-Eintrag
ord-174b0e6d08be43ed8f6d955616f7ed91
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367666B2

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