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

HRID 22603

Reaktionsgleichung

Reaktionsgleichung von HRID 22603
[Si]([O:18][CH2:19][C:20]1[CH:21]=[C:22]([CH:26]([S:34][CH2:35][CH2:36][C:37](=[O:41])[N:38]([CH3:40])[CH3:39])[S:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH:23]=[CH:24][CH:25]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>C1COCC1>[OH:18][CH2:19][C:20]1[CH:21]=[C:22]([CH:26]([S:34][CH2:35][CH2:36][C:37](=[O:41])[N:38]([CH3:40])[CH3:39])[S:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH:23]=[CH:24][CH:25]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 85324336(+)-Methyl 5-(3-(t-butyldiphenylsilyloxymethyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of (-)-methyl 5-(3-(t-butyldiphenylsilyloxymethyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate (step 5) (1.377 g, 2.26 mmol.) in THF (25 mL ) a t room temperature was slowly added tetra-n-butyl ammonium fluoride (1M) in THF (2.34 mL). The solution was stirred 2 hrs at room temperature Ethyl acetate was added to the reaction mixture, and the organic layer 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. customa t room temperature
  2. additionwas added to the reaction mixture
  3. washthe organic layer it was 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-2bb48eda672e47808d847e85d1bb59cf
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428171

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