Dimethyl Sulfoxide → HCID 59985490, compound

HRID 23934Notes

Reaction equation

HRID 23934 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 59985490HCID 59985490, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-2632265afe964a43bf960e376dbd2309
Source dataset
uspto-grants-2005_02
Patent number
US06855724B2

Reaction notes

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