1,2-Diiodoethane → 17-Ethyl-1,2,14-trihydroxy-12-[2'-(4"-(naphth-2-yl)-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-3,10,16-trione

HRID 865568

반응식

HRID 865568 반응식
ICCI.[Sm].C(=O)=O.CC(C)=O.[CH2:13]([CH:15]1[CH:41]=[C:40]([CH3:42])[CH2:39][CH:38]([CH3:43])[CH2:37][CH:36]([O:44][CH3:45])[CH:35]2[O:46][C:31]([OH:50])([CH:32]([CH3:49])[CH2:33][CH:34]2[O:47][CH3:48])[C:30](=[O:51])[C:29](=[O:52])[N:28]2[CH:23]([CH2:24][CH2:25][CH2:26][CH2:27]2)[C:22](=[O:53])[O:21][CH:20]([C:54]([CH3:74])=[CH:55][CH:56]2[CH2:61][CH2:60][CH:59]([C:62]3[CH:71]=[CH:70][C:69]4[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=4)[CH:63]=3)[CH:58]([O:72][CH3:73])[CH2:57]2)[CH:19]([CH3:75])[CH:18]([OH:76])[CH2:17][C:16]1=[O:77])[CH3:14]>C1COCC1.C1COCC1.CO>[CH2:13]([CH:15]1[CH:41]=[C:40]([CH3:42])[CH2:39][CH:38]([CH3:43])[CH2:37][CH:36]([O:44][CH3:45])[CH:35]2[O:46][C:31]([OH:50])([CH:32]([CH3:49])[CH2:33][CH:34]2[O:47][CH3:48])[CH:30]([OH:51])[C:29](=[O:52])[N:28]2[CH:23]([CH2:24][CH2:25][CH2:26][CH2:27]2)[C:22](=[O:53])[O:21][CH:20]([C:54]([CH3:74])=[CH:55][CH:56]2[CH2:61][CH2:60][CH:59]([C:62]3[CH:71]=[CH:70][C:69]4[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=4)[CH:63]=3)[CH:58]([O:72][CH3:73])[CH2:57]2)[CH:19]([CH3:75])[CH:18]([OH:76])[CH2:17][C:16]1=[O:77])[CH3:14]

참가 물질

7

반응물 4

HCID 122241,2-DiiodoethaneHCID 23951SamariumHCID 18522661Acetone cardiceHCID 5718413317-Ethyl-1,14-dihydroxy-12-[2'-(4"-(naphth-2-yl)-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone

생성물 1

HCID 5712063717-Ethyl-1,2,14-trihydroxy-12-[2'-(4"-(naphth-2-yl)-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-3,10,16-trione수율 22.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 21899815MeOH tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

A solution of 1,2-diiodoethane (42 mg, 0.15 mmol) in dry THF (1 mL) was added dropwise to a stirred mixture of samarium metal (46.5 mg, 0.31 mmol) in dry THF (1 mL) and stirred for 1.5 hours. The reaction mixture was then cooled to -78° C. (dry ice/acetone) and treated with a solution of 17-ethyl-1,14-dihydroxy-12-[2'-(4"-(naphth-2-yl)-3"-methoxycyclohexyl)-1 '-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (100 mg, 0.109 mmol) in 1:1 THF/CH3OH. The mixture was maintained at -78° C. for 15 minutes then allowed to warm to room temperature. The reaction was quenched with cold saturated aqueous K2CO3 and quickly extracted with CH2Cl2. The extracts were combined, dried with Na2SO4, filtered and concentrated in vacuo. Purified by preparative TLC on silica gel (eluted with 7% CH3OH in CH2Cl2) to give 22 mg of 17-ethyl-1,2,14-trihydroxy-12-[2'-(4"-(naphth-2-yl)-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-3,10,16-trione (1H NMR and mass spectral analysis are consistent with the desired structure).

후처리

  1. temperatureto warm to room temperature
  2. customThe reaction was quenched with cold saturated aqueous K2CO3
  3. extractionquickly extracted with CH2Cl2
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurified by preparative TLC on silica gel (eluted with 7% CH3OH in CH2Cl2)

출처 및 근거

ORD 기록
ord-4a4b0ffbe16c49c2ac988f2403f5d38c
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05565560

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