Dimethyl Sulfoxide → HCID 59985490, Verbindung

HRID 1351231Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1351231
[F:1][C:2]1[CH:3]=[C:4]([C@@H:8]([NH:12][C:13](=[O:15])[CH3:14])[CH2:9][CH2:10][OH:11])[CH:5]=[CH:6][CH:7]=1.CS(C)=O.C(N(CC)CC)C>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C@@H:8]([NH:12][C:13](=[O:15])[CH3:14])[CH2:9][CH:10]=[O:11])[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 59985487N-[(1S)-1-(3-Fluorophenyl)-3-hydroxypropyl]acetamide

Produkt 1

HCID 59985490HCID 59985490, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Pyridine sulfur trioxide complex (37.7 g, 237 mmol) was added portionwise over 20 minutes to a stirred cold (0° C.) solution of N-[(1S)-1-(3-fluorophenyl)-3-hydroxypropyl]acetamide (25 g, 118 mmol), DMSO (16.5 ml, 233 mmol) and triethylamine (33 ml, 237 mmol) in dichloromethane (240 ml). After two hours stirring at room temperature, solvent was evaporated under reduced pressure and the residue applied directly to a silica gel column. Eluting with a gradient system starting with ethyl acetate:dichloromethane (50:50 by volume) then ethyl acetate:dichloromethane (80:20 by volume) and finally ethyl acetate gave the title compound as a colourless oil which solidified on standing (13.9 g).

Aufarbeitung

  1. customsolvent was evaporated under reduced pressure
  2. washEluting with a gradient system

Quellen und Nachweise

ORD-Eintrag
ord-fda3c927b83f465a8fc29467350c269c
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07217721B2

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