Dimethyl Sulfoxide → HCID 18657624, compound

HRID 2397018Notes

Reaction equation

HRID 2397018 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[F:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[C@:19]([OH:35])([C@H:26]([N:28]1[CH:32]=[C:31]([CH2:33][OH:34])[N:30]=[N:29]1)[CH3:27])[CH2:20][N:21]1[CH:25]=[N:24][CH:23]=[N:22]1.[Cl-].[NH4+]>ClCCl.C(N(CC)CC)C>[F:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[C@:19]([OH:35])([C@H:26]([N:28]1[CH:32]=[C:31]([CH:33]=[O:34])[N:30]=[N:29]1)[CH3:27])[CH2:20][N:21]1[CH:25]=[N:24][CH:23]=[N:22]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 53770267HCID 53770267, compound

Product 1

HCID 18657624HCID 18657624, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

Dimethylsulfoxide (1.08 ml) was added dropwise at -78° C. to a solution of oxalyl chloride (1 ml) in dichloromethane (30 ml), followed by stirring for 10 minutes. To the mixture was added dropwise over the period of 5 minutes a solution of (2R,3R)-2-(2,4-difluorophenyl)-3-(4-hydroxymethyl-1H-1,2,3-triazol-1-yl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (2 g) in dichloro-methane (30 ml), followed by stirring for 15 minutes at -78° C. and then for 1 hour at -45° C. To the mixture was added triethylamine (5 ml), followed by stirring for 20 minutes at 0° C. To the mixture was added a saturated aqueous ammonium chloride solution (20 ml). The mixture was extracted with dichloromethane (40 ml). The extract was dried over anhydrous magnesium sulfate and distilled under reduced pressure. The residue was purified by silica gel chromatography (silica gel: 200 g, eluent: ethyl acetate/dichloromethane=3:1) to give Compound 71 (1.49 g), which was crystallized from diisopropyl ether to yield a colorless crystalline powder.

Workup

  1. stirringby stirring for 15 minutes at -78° C.
  2. waitfor 1 hour at -45° C
  3. stirringby stirring for 20 minutes at 0° C
  4. extractionThe mixture was extracted with dichloromethane (40 ml)
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customThe residue was purified by silica gel chromatography (silica gel: 200 g, eluent: ethyl acetate/dichloromethane=3:1)

Sources & evidence

ORD record
ord-2dd1282c5644411dbb916714d171b688
Source dataset
uspto-grants-1996_02
Patent number
US05495024

Reaction notes

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