Oxalyl chloride → HCID 178468298, compound

HRID 1797011Notes

Reaction equation

HRID 1797011 reaction equation
C(Cl)(=O)C(Cl)=O.[OH:7][CH:8]([CH3:31])[CH2:9][NH:10][C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19]2[NH:20][CH:21]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Br:30])[CH:25]=3)[N:23]=2)[CH2:15][CH2:14]1)=[O:12]>C(Cl)Cl.CS(C)=O.O>[O:7]=[C:8]([CH3:31])[CH2:9][NH:10][C:11]([C@H:13]1[CH2:14][CH2:15][C@H:16]([C:19]2[NH:20][CH:21]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Br:30])[CH:25]=3)[N:23]=2)[CH2:17][CH2:18]1)=[O:12]

Participants

6

Reactant 2

HCID 65578Oxalyl chlorideHCID 178468299HCID 178468299, compound

Product 1

HCID 178468298HCID 178468298, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a cooled solution (−78° C. to −60° C.) of oxalyl chloride (0.12 mmol) in CH2Cl2 (5 mL), DMSO (0.25 mmoL) was added dropwise. The mixture was stirred for 2 minutes, and then trans-4-[4-(3-bromo-phenyl)-1H-imidazol-2-yl]-cyclohexane-carboxylic acid (2-hydroxy-propyl) amide (0.12 mmol) in 2 ml of CH2Cl2 was added. The mixture was stirred for 15 minutes at the same temperature following the addition of TEA (0.60 mmol). The mixture was stirred for another 5 minutes, warmed to room temperature and diluted with water. The organic layer was isolated, dried over Na2SO4, concentrated under vacuum, and purified with flash chromatography (90:10:1 CH2Cl2/MeOH/NH4OH) to give trans-4-[4-(3-bromo-phenyl)-1H-imidazol-2-yl]-cyclohexane-carboxylic acid (2-oxo-propyl) amide.

Workup

  1. stirringThe mixture was stirred for 15 minutes at the same temperature
  2. stirringThe mixture was stirred for another 5 minutes
  3. customThe organic layer was isolated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. custompurified with flash chromatography (90:10:1 CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-ceab955539074d8088d313274eb19274
Source dataset
uspto-grants-2006_04
Patent number
US07034034B2

Reaction notes

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