Dimethyl Sulfoxide → HCID 57868868, compound

HRID 1966136Notes

Reaction equation

HRID 1966136 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]1([S:15]([N:18]2[CH2:21][CH:20]([OH:22])[CH2:19]2)(=[O:17])=[O:16])[CH2:14][CH2:13]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:11][C:12]1([S:15]([N:18]2[CH2:19][C:20](=[O:22])[CH2:21]2)(=[O:17])=[O:16])[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 57868833HCID 57868833, compound

Product 1

HCID 57868868HCID 57868868, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (59 μL, 0.69 mmol) in methylene chloride (1.5 mL) at −78° C. was added dimethyl sulfoxide (0.10 mL, 1.5 mmol) slowly dropwise. The reaction was stirred for 15 minutes following complete addition. A solution of 1-[(1-methylcyclopropyl)-sulfonyl]azetidin-3-ol (64 mg, 0.33 mmol) in methylene chloride (1.0 mL) was added dropwise and the reaction mixture was stirred for 45 min at −60° C. Triethylamine (0.28 mL, 2.0 mmol) was added dropwise and the reaction was stirred for 15 minutes and the bath was removed and the solution allowed to warm to ambient temperature. The solvent was removed in vacuo and ethyl acetate was added. The solution was washed sequentially with saturated sodium bicarbonate solution, water and brine, dried over sodium sulfate, decanted and concentrated. The crude product was used without further purification in Step 6.

Workup

  1. additionaddition
  2. stirringthe reaction mixture was stirred for 45 min at −60° C
  3. stirringthe reaction was stirred for 15 minutes
  4. customthe bath was removed
  5. customThe solvent was removed in vacuo and ethyl acetate
  6. additionwas added
  7. washThe solution was washed sequentially with saturated sodium bicarbonate solution, water and brine
  8. dry with materialdried over sodium sulfate
  9. customdecanted
  10. concentrationconcentrated
  11. customThe crude product was used without further purification in Step 6

Sources & evidence

ORD record
ord-a295554a78e74782aadab76fc58ee3d2
Source dataset
uspto-grants-2013_04
Patent number
US08420629B2

Reaction notes

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