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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
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 865568
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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 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

Produkt 1

HCID 57120637
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
Ausbeute 22,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 21899815MeOH tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-4a4b0ffbe16c49c2ac988f2403f5d38c
Quelldatensatz
uspto-grants-1996_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05565560

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