Pyridine, hydrofluoride (1:1) → 17-Ethyl-1,14-dihydroxy-12-[2'-(4"-(2'"-phenyl-2'"-benzyloxyethyloxy)-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

HRID 1939111Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1939111
[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:69])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([O:50][CH2:51][CH:52]([C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[O:53][CH2:54][C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[CH:46]([O:67][CH3:68])[CH2:45]2)[CH:7]([CH3:70])[CH:6]([O:71][Si](C(C)(C)C)(C)C)[CH2:5][C:4]1=[O:79])[CH3:2].C1C=CN=CC=1.F>C1COCC1>[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:69])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([O:50][CH2:51][CH:52]([C:61]3[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=3)[O:53][CH2:54][C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[CH:46]([O:67][CH3:68])[CH2:45]2)[CH:7]([CH3:70])[CH:6]([OH:71])[CH2:5][C:4]1=[O:79])[CH3:2]

Komponenten

4

Edukt 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 13171945217-Ethyl-1-hydroxy-14-(tert-butyldimethylsiloxy)-12-[2'-(4"-(2"'-phenyl-2"'-benzyloxyethyloxy)-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 5713333517-Ethyl-1,14-dihydroxy-12-[2'-(4"-(2'"-phenyl-2'"-benzyloxyethyloxy)-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-tetraoneAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of the product from Step A (22 mg) in THF (100 μl) was added hydrogen fluoride/pyridine and the reaction stirred at room temperature for 6 hours. The reaction was then quenched by the addition of saturated aqueous sodium bicarbonate and extracted into ethyl acetate. The organic phase was dried with magnesium sulphate and concentrated. The crude material was purified by column chromatography on silica gel eluting with 50% hexane:50% ethyl acetate to give the title compound (15 mg).

Aufarbeitung

  1. customThe reaction was then quenched by the addition of saturated aqueous sodium bicarbonate
  2. extractionextracted into ethyl acetate
  3. dry with materialThe organic phase was dried with magnesium sulphate
  4. concentrationconcentrated
  5. customThe crude material was purified by column chromatography on silica gel eluting with 50% hexane

Quellen und Nachweise

ORD-Eintrag
ord-5e799e001616468885e6f3f7a7baf385
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05693648

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