Ethyl Acetate → HCID 86604546, 화합물

HRID 1446644노트

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HRID 1446644 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C(OC(O[CH:17]1[CH2:29][CH2:28][C:27]([O:31][CH:32]([O:34][CH2:35][CH3:36])[CH3:33])([CH3:30])[CH:26]([OH:37])[CH:25]=[CH:24][CH:23]([CH3:38])[CH:22](/[C:39](/[CH3:60])=[CH:40]/[CH:41]=[CH:42]/[CH:43]([CH3:59])[CH2:44][CH:45]2[O:58][CH:46]2[CH:47]([CH3:57])[CH:48]([O:51][CH:52]([O:54][CH2:55][CH3:56])[CH3:53])[CH2:49][CH3:50])[O:21][C:19](=[O:20])[CH2:18]1)C)C.Cl.C(Cl)(=O)C1C=CC=NC=1.C(OCC)(=O)C>O1CCCC1.O1CC(CCN)C(CCN)C1CCN.O>[CH2:35]([O:34][CH:32]([O:31][C:27]1([CH3:30])[CH:26]([OH:37])[CH:25]=[CH:24][CH:23]([CH3:38])[CH:22](/[C:39](/[CH3:60])=[CH:40]/[CH:41]=[CH:42]/[CH:43]([CH3:59])[CH2:44][CH:45]2[O:58][CH:46]2[CH:47]([CH3:57])[CH:48]([O:51][CH:52]([O:54][CH2:55][CH3:56])[CH3:53])[CH2:49][CH3:50])[O:21][C:19](=[O:20])[CH:18]=[CH:17][CH2:29][CH2:28]1)[CH3:33])[CH3:36]

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 2733832Lithium HexamethyldisilazideHCID 21023947(8E,12E,14E)-3,6,21-Tri(1-ethoxyethoxy)-7-hydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide

생성물 1

HCID 86604546HCID 86604546, 화합물수율 67%

시약·촉매·용매 3

HCID 68666183HCID 68666183, 화합물촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Lithium bis(trimethylsilyl)amide (1.0 M tetrahydrofuran solution, 50 μL, 50 μmol) was added dropwise to a solution of (8E,12E,14E)-3,6,21-tri(1-ethoxyethoxy)-7-hydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (10.8 mg, 15.2 μmol) in tetrahydrofuran (2 mL) at −40° C. under nitrogen atmosphere, followed by stirring at the same temperature for 20 min. Then, a solution of nicotinoyl chloride hydrochloride (5.7 mg, 30.4 μmol) in tetrahydrofuran-triethylamine (tetrahydrofuran: 0.5 mL and triethyamine: 1 drop) was added dropwise thereinto, followed by stirring at 0° C. for 30 min. Ethyl acetate and water were added to the reaction solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered and then evaporated. The resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm; ethyl acetate-hexane=1:4) to obtain the title compound (6.3 mg, 67%) as a colorless oil.

후처리

  1. stirringby stirring at 0° C. for 30 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm; ethyl acetate-hexane=1:4)

출처 및 근거

ORD 기록
ord-3e2c924abf374222ab56b653f2426e6e
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07667052B2

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