Dimethyl Sulfoxide → HCID 19002303, compound

HRID 2260012Notes

Reaction equation

HRID 2260012 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:13][O:14][P:15]([CH:21]([OH:42])[C:22]1[CH:41]=[CH:40][C:25]([CH2:26][CH:27]([C:36]([O:38][CH3:39])=[O:37])[NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:24][CH:23]=1)([O:17][O:18][CH2:19][CH3:20])=[O:16])[CH3:12].CCN(CC)CC>C(Cl)Cl>[CH2:19]([O:18][O:17][P:15]([C:21](=[O:42])[C:22]1[CH:41]=[CH:40][C:25]([CH2:26][CH:27]([C:36]([O:38][CH3:39])=[O:37])[NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:30])=[CH:24][CH:23]=1)([O:14][O:13][CH2:11][CH3:12])=[O:16])[CH3:20]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19002308HCID 19002308, compound

Product 1

HCID 19002303HCID 19002303, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
-78 °C

Procedure

To a solution of oxalyl chloride (371 μL, 548 mg, 4.32 mmol, 2 equivalents) in anhydrous CH2Cl2 (8 mL) at -78° C. under argon was added anhydrous DMSO (612 μL, 674 mg, 8.64 mmol, 4 equivalents) in anhydrous CH2Cl2 (8 mL) dropwise over 17 minutes. To the resulting clear, colorless solution was added 40 (961 mg, 2.16 mmol) in anhydrous CH2Cl2 (8 mL) dropwise at -78° C. over 15 minutes. The reaction was stirred at -78° C. (45 minutes) then NEt3 (3.00 mL, 2.18 g, 21.6 mmol, 10 equivalents) in anhydrous CH2Cl2 (8 mL) was added dropwise at -78° C. over 10 minutes. The resulting clear, light yellow solution was stirred at 0° C. (50 minutes), then shaken well with ice-cold 0.2 N HCl/brine (100 mL); extracted with EtOAc (3×75 mL); washed with ice-cold 0.2 N HCl/brine (2×50 mL); brine (2×100 mL); dried (MgSO4) and rotovapped (20° C.) once from CHCl3, then twice from CH2Cl2 and placed under high vacuum, yielding 41 as an oil (962 mg, 100%).

Workup

  1. stirringThe resulting clear, light yellow solution was stirred at 0° C. (50 minutes)
  2. extractionextracted with EtOAc (3×75 mL)
  3. washwashed with ice-cold 0.2 N HCl/brine (2×50 mL)
  4. dry with materialdried (MgSO4)
  5. custom(20° C.)

Sources & evidence

ORD record
ord-6338db9d45d449888b450bebf74f033f
Source dataset
uspto-grants-1995_12
Patent number
US05475129

Reaction notes

Loading…