Methanol → HCID 86746112, Verbindung

HRID 1885425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1885425
C([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](O)([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]([CH3:63])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([O:50][Si](C(C)C)(C(C)C)C(C)C)[CH:46]([O:61][CH3:62])[CH2:45]2)[CH:7]([CH3:64])[CH:6]([O:65][Si:66]([CH:73]([CH3:75])[CH3:74])([CH:70]([CH3:72])[CH3:71])[CH:67]([CH3:69])[CH3:68])[CH2:5][C:4]1=[O:76])C.CO.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CCCCCC.C(OCC)(=O)C>C(Cl)Cl>[CH:73]([Si:66]([CH:67]([CH3:69])[CH3:68])([CH:70]([CH3:72])[CH3:71])[O:65][CH:6]1[CH2:5][C:4](=[O:76])[CH2:3][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][CH:19]([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]([CH3:63])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([OH:50])[CH:46]([O:61][CH3:62])[CH2:45]2)[CH:7]1[CH3:64])([CH3:74])[CH3:75]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 21226206Ethyl acetate hexaneHCID 5720084217-Ethyl-1-hydroxy-12-[2'-(4"-triisopropylsilyloxy-3"-methoxycyclohexyl)-1'-methylvinyl]-14-triisopropylsilyloxy-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 86746112HCID 86746112, VerbindungAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

17-Ethyl-1-hydroxy-14-triisopropylsilyloxy-12-[2'-(4"-triisopropylsilyloxy-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 (8.98 g, 8.14 mmol) was slowly added to methanol (70 ml) containing p-toluenesulfonic acid monohydrate (0.70 g). The compound slowly dissolved and after 2 hr. TLC hexane/ethyl acetate (3:1) indicated no starting material was present. The reaction mixture was diluted to 250 ml with MeCl2 and washed with saturated aqueous NaHCO3 (250 ml). The organic layer was separated and the aqueous layer was extracted with additional MeCl2. The combined organic extracts were washed with brine and dried over magnesium sulfate. After evaporation in vacuo, the residue was chromatographed over SiO2 and eluted with MeCl2 /isopropanol (100:3) to yield 17-ethyl-1-hydroxy, 14-triisopropylsilyloxy-12-[2'-(4"-hydroxy-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 (6.77 g, 87.9%). Mass Spec: C52H88NO12Si (948.37) FAB+Li:955 (M+Li), 721, 695, 676, 553, 266.

Aufarbeitung

  1. dissolutionThe compound slowly dissolved and after 2 hr
  2. washwashed with saturated aqueous NaHCO3 (250 ml)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with additional MeCl2
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customAfter evaporation in vacuo
  8. customthe residue was chromatographed over SiO2
  9. washeluted with MeCl2 /isopropanol (100:3)

Quellen und Nachweise

ORD-Eintrag
ord-9a798bdc100343bb9f315be50cc24340
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05143918

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