Dimethyl Sulfoxide → HCID 86656230, compound

HRID 1629746Notes

Reaction equation

HRID 1629746 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C@H:18]([NH:21][C:22]2[CH:23]=[C:24]([CH:29]=[O:30])[C:25]([CH3:28])=NC=2)[CH2:19][CH3:20])=[CH:14][C:13]=1[CH3:31].C[CH2:33][N:34](CC)CC>C(Cl)Cl>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C@H:18]([NH:21][C:22]2[CH:23]=[C:24]([CH:29]=[O:30])[C:25]([CH3:28])=[CH:33][N:34]=2)[CH2:19][CH3:20])=[CH:14][C:13]=1[CH3:31]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86656229HCID 86656229, compound

Product 1

HCID 86656230HCID 86656230, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

Oxalyl chloride (0.232 mL, 2.70 mmol) was dissolved in CH2Cl2 (15 mL) and the solution was cooled to −78° C. A solution of DMSO (0.383 mL, 5.40 mmol) in CH2Cl2 (3 mL) was added dropwise and the mixture was stirred for 10 minutes at this temperature. Then, a solution of INT 55 (329 mg, 1.079 mmol) in CH2Cl2 (3 mL) was added dropwise and the mixture was stirred for 1 hour at this temperature. NEt3 (0.932 mL, 6.69 mmol) was added and the mixture was stirred further at −78° C. for 1 hour and the mixture was quenched with water. The mixture was poured onto 10% aqueous KHSO4 and extracted with EtOAc. The organic layer was washed with saturated aqueous sodium bicarbonate solution and brine, dried over sodium sulfate, filtered and concentrated. The product was used in the next step without further purification.

Workup

  1. stirringthe mixture was stirred for 1 hour at this temperature
  2. stirringthe mixture was stirred further at −78° C. for 1 hour
  3. customthe mixture was quenched with water
  4. additionThe mixture was poured onto 10% aqueous KHSO4
  5. extractionextracted with EtOAc
  6. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-018031de50054e45ba19f665c41ef9e8
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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