Tetrahydrofuran → (+)-Methyl 5-(3-(hydroxymethyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate

HRID 232433

Reaktionsgleichung

Reaktionsgleichung von HRID 232433
[Si](OCC1C=C([CH:26]([S:31][CH2:32][S:33][CH2:34][CH2:35][C:36](=[O:40])[N:37]([CH3:39])[CH3:38])CC([O-])=O)C=CC=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].[CH2:42]([N+](CCCC)(CCCC)CCCC)[CH2:43][CH2:44]C.[C:59]([O:62][CH2:63]C)(=[O:61])[CH3:60].[CH2:65]1[CH2:69][O:68][CH2:67][CH2:66]1>>[OH:68][CH2:67][C:66]1[CH:65]=[C:69]([CH:32]([S:33][CH2:34][CH2:35][C:36](=[O:40])[N:37]([CH3:38])[CH3:39])[S:31][CH2:26][CH2:60][C:59]([O:62][CH3:63])=[O:61])[CH:42]=[CH:43][CH:44]=1

Komponenten

5

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 1317160153-(3-(t-Butyldiphenylsilyloxymethyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate

Produkt 1

HCID 19930508(+)-Methyl 5-(3-(hydroxymethyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate

Versuchsvorschrift

To a solution of (+)-methyl 5-(3-(3-(t-butyldiphenylsilyloxymethyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate (step 1) (1.377 g, 2.26 mmol.) in THF (25 mL) at room temperature was slowly added tetra-n-butylammonium fluoride 1M in THF (2.34 mL). The solution was stirred 2 hrs at room temperature Ethyl acetate was added to the reaction mixture, it was washed with brine (3×), dried over sodium sulfate, filtered and evaporated to dryness. Purification by flash chromatography using 40% acetone in hexane afforded the title compound.

Aufarbeitung

  1. customat room temperature
  2. additionwas added to the reaction mixture, it
  3. washwas washed with brine (3×)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-18c02aae23b9499a8edc99c41bf5d64d
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04851409

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