Triethylamine → HCID 86602614, 화합물

HRID 1987546노트

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HRID 1987546 반응식
[C:1]([O:4][CH:5]1[C:6]([OH:39])([CH3:38])[CH2:7][CH2:8][CH:9]([OH:37])[CH2:10][C:11]([O:13][CH:14](/[C:19](/[CH3:36])=[CH:20]/[CH:21]=[CH:22]/[C:23]([OH:35])([CH3:34])[CH2:24][CH:25]2[O:33][CH:26]2[CH:27]([CH3:32])[CH:28]([OH:31])[CH2:29][CH3:30])[CH:15]([CH3:18])[CH:16]=[CH:17]1)=[O:12])(=[O:3])[CH3:2].C(N([CH2:45][CH3:46])CC)C.Cl[Si:48]([CH2:53][CH3:54])([CH2:51][CH3:52])[CH2:49][CH3:50]>ClCCl.C(OCC)(=O)C>[C:1]([O:4][CH:5]1[C:6]([OH:39])([CH3:38])[CH2:7][CH2:8][CH:9]([O:37][Si:48]([CH2:45][CH3:46])([CH2:51][CH3:52])[CH2:49][CH3:50])[CH2:10][C:11]([O:13][CH:14](/[C:19](/[CH3:36])=[CH:20]/[CH:21]=[CH:22]/[C:23]([OH:35])([CH3:34])[CH2:24][CH:25]2[O:33][CH:26]2[CH:27]([CH3:32])[CH:28]([O:31][Si:48]([CH2:53][CH3:54])([CH2:51][CH3:52])[CH2:49][CH3:50])[CH2:29][CH3:30])[CH:15]([CH3:18])[CH:16]=[CH:17]1)=[O:12])(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 13819ChlorotriethylsilaneHCID 10007797Pladienolide D

생성물 1

HCID 86602614HCID 86602614, 화합물수율 102.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

A solution of (8E,12E,14E)-7-acetoxy-3,6,16,21-tetrahydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (221 mg, 0.4 mmol), N,N-dimethylaminopyridine (25 mg, 0.2 mmol) and triethylamine (613 mg, 6 mmol) in dichloromethane (7 mL) was cooled to 5° C., a solution of chlorotriethylsilane (609 mg, 4 mmol) in dichloromethane (3 mL) was added dropwise thereto, and the reaction mixture was stirred at room temperature for one hour. The reaction mixture was diluted with ethyl acetate, washed with water and a saturated aqueous solution of sodium bicarbonate, dried over anhydrous magnesium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm; ethyl acetate-hexane, 1:9 to 1:4 to 1:3) to give the title compound (320 mg, quantitative) as a colorless oil.

후처리

  1. washwashed with water
  2. dry with materiala saturated aqueous solution of sodium bicarbonate, dried over anhydrous magnesium sulfate
  3. customevaporated
  4. customThe resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm; ethyl acetate-hexane, 1:9 to 1:4 to 1:3)

출처 및 근거

ORD 기록
ord-e710355e9cc443a690d3a0e4ab0e8e5d
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07550503B2

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