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

반응식

HRID 383547 반응식
[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

참가 물질

6

반응물 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

생성물 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)-amide수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.).

후처리

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

출처 및 근거

ORD 기록
ord-174b0e6d08be43ed8f6d955616f7ed91
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367666B2

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