Dimethyl Sulfoxide → HCID 53952975, compound

HRID 1459405Notes

Reaction equation

HRID 1459405 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]12([NH:21][C:22](=[O:40])[C:23]([CH2:38][OH:39])([CH2:31][C:32]3[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=3)[CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2.C(N(CC)CC)C>C(Cl)Cl>[C:11]12([NH:21][C:22](=[O:40])[C:23]([CH:38]=[O:39])([CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[CH2:31][C:32]3[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=3)[CH2:12][CH:13]3[CH2:14][CH:15]([CH2:16][CH:17]([CH2:19]3)[CH2:18]1)[CH2:20]2

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 53924158HCID 53924158, compound

Product 1

HCID 53952975HCID 53952975, compoundYield 163.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a well-stirred dry ice/acetone bath chilled solution of oxalyl chloride (163,μl, 1.91 mmol) in methylene chloride (4.5 ml), a solution of dimethyl sulfoxide (259 μl, 3.6 mmol) in methylene chloride (2.25 ml) was added dropwise while maintaining the temperature below -55° C. After stirring the reaction at that temperature for 5 minutes, N-adamantan-1-yl-2-hydroxymethyl-3-pyridin-4-yl-2-pyridin-4-ylmethyl-propion-amide (700 mg, 1.73 mmol) in methylene chloride (2.25 ml) was added, and the reaction was stirred for 30 minutes. Triethylamine (1.20 ml, 8.65 mmol) was added, and the reaction was stirred for 5 minutes before removing the cooling bath. After stirring for 20 minutes at ambient temperature, the reaction was quenched by addition to water/methylene chloride (40 ml of each). The mixture was then extracted three times with 40 ml portions of methylene chloride. The combined extracts were dried (anhydrous sodium sulfate) and concentrated in vacuo to afford a yellow oil (1.14 g). Flash chromatography of the entire sample (silica gel, 40 micron mesh; elution initially with methanol/methylene chloride=3:97 in volume, and increasing the methanol concentration during elution finally to methanol/methylene chloride=1:9 in volume) afforded the title compound (475 mg) as an oil.

Workup

  1. temperaturewhile maintaining the temperature below -55° C
  2. customthe reaction at that temperature for 5 minutes
  3. stirringthe reaction was stirred for 30 minutes
  4. stirringthe reaction was stirred for 5 minutes
  5. custombefore removing the cooling bath
  6. stirringAfter stirring for 20 minutes at ambient temperature
  7. customthe reaction was quenched by addition to water/methylene chloride (40 ml of each)
  8. extractionThe mixture was then extracted three times with 40 ml portions of methylene chloride
  9. dry with materialThe combined extracts were dried (anhydrous sodium sulfate)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-edccb64bece64b9dad9d0fa1360b7f87
Source dataset
uspto-grants-1998_12
Patent number
US05854232

Reaction notes

Loading…