Dimethyl Sulfoxide → HCID 11172300, compound

HRID 538671Notes

Reaction equation

HRID 538671 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[CH2:24][CH2:25][CH2:26][OH:27])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(CC)CC>C(Cl)Cl.O>[CH2:11]([N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[CH2:24][CH2:25][CH:26]=[O:27])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 11322245HCID 11322245, compound

Product 1

HCID 11172300HCID 11172300, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (0.55 mL, 6.44 mmol) was added to a stirred solution of DMSO (0.92 mL, 12.87 mmol) in dry DCM (40 mL) at −78° C. and the reaction mixture was stirred for 15 minutes. Compound 22 (1 g, 4.29 mmol) dissolved in DCM (15 mL) was the added drop-wise and the reaction mixture was stirred at −78° C. for 1 hour. The reaction mixture was then quenched by adding Et3N (2.9 mL, 21.45 mmol) drop-wise and the solution was stirred at rt for 15 minutes. Water was then added to the solution and the reaction mixture was extracted with DCM. The organic layer was dried over Na2SO4, filtered and concentrated to yield crude compound 23 which was used as such for the next step.

Workup

  1. stirringthe reaction mixture was stirred at −78° C. for 1 hour
  2. customThe reaction mixture was then quenched
  3. stirringthe solution was stirred at rt for 15 minutes
  4. extractionthe reaction mixture was extracted with DCM
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-82468703facb4f9e94ce547dc6cd11f3
Source dataset
uspto-grants-2014_10
Patent number
US08865741B2

Reaction notes

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