Dimethyl Sulfoxide → HCID 15538398, compound

HRID 2205174Notes

Reaction equation

HRID 2205174 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([O:18][C@H:19]1[C@@H:26]2[C@@H:22]([O:23][C:24]([CH3:28])([CH3:27])[O:25]2)[O:21][C@:20]1([CH2:38][OH:39])[CH2:29][O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[CH2:11]([O:18][C@H:19]1[C@@H:26]2[C@@H:22]([O:23][C:24]([CH3:28])([CH3:27])[O:25]2)[O:21][C@@:20]1([CH2:29][O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH:38]=[O:39])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 11732122HCID 11732122, compound

Product 1

HCID 15538398HCID 15538398, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

DMSO (1.65 mL, 23.6 mmol) was added drop-wise to a cold (−78° C.) solution of oxalyl chloride (1.05 mL, 12.0 mmol) in dichloromethane (50 mL). After stirring for 30 min, a solution of compound 2 (3 g, 7.5 mmol) in dichloromethane (25 mL) was added to the reaction. The stirring was continued for 45 min at −78° C., and triethylamine (3.5 mL, 25.0 mmol) was added to the reaction. The reaction was stirred at −78° C. for 15 min, after which the ice-bath was removed and the reaction was allowed to gradually warm over 45 min. The reaction was diluted with dichloromethane and the organic phase was sequentially washed with 5% aqueous HCl solution, saturated aqueous NaHCO3 solution, brine, dried (Na2SO4) and concentrated under reduced pressure to provide 3 (2.2 g, crude), which was used without any further purification. LC-MS (M+H)+=399.1

Workup

  1. waitThe stirring was continued for 45 min at −78° C.
  2. stirringThe reaction was stirred at −78° C. for 15 min
  3. customafter which the ice-bath was removed
  4. temperatureto gradually warm over 45 min
  5. additionThe reaction was diluted with dichloromethane
  6. washthe organic phase was sequentially washed with 5% aqueous HCl solution, saturated aqueous NaHCO3 solution, brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure
  9. customto provide 3 (2.2 g, crude), which
  10. customwas used without any further purification

Sources & evidence

ORD record
ord-ebaabeffd35c4944b4158e741c75498e
Source dataset
uspto-grants-2016_06
Patent number
US09370569B2

Reaction notes

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