Methanesulfonyl chloride → HCID 24785041, compound

HRID 1717509Notes

Reaction equation

HRID 1717509 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:6]([N:8]([CH2:12][C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=2[O:21][CH2:22][CH2:23][OH:24])[C:9](=[O:11])[CH3:10])[CH:7]=1.C(N(C(C)C)CC)(C)C.[S:41](Cl)([CH3:44])(=[O:43])=[O:42]>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[C:6]([N:8]([CH2:12][C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=2[O:21][CH2:22][CH2:23][O:24][S:41]([CH3:44])(=[O:43])=[O:42])[C:9](=[O:11])[CH3:10])[CH:7]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 24785043HCID 24785043, compound

Product 1

HCID 24785041HCID 24785041, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 300 mg (0.71 mmol) 1e and 139 mg (1.06 mmol) diisopropyl ethyl amine in 5 ml dichloromethane was added 97 mg (0.85 mmol) mesyl chloride in 0.5 ml dichloromethane drop wisely at −10° C. The stirred reaction mixture was warmed over a period of 4 h to room temperature and diluted with dichloromethane. The organic phase was washed with saturated sodium hydrogen carbonate solution, water and brine. The organic phase was dried with magnesium sulfate. The crude product was purified by silica column chromatography (ethyl acetate:hexane gradient 1:6→1:2). The desired product 1f was obtained in 88% yield (346 mg, 0.62 mmol) as yellow oil.

Workup

  1. customThe stirred reaction mixture
  2. temperaturewas warmed over a period of 4 h to room temperature
  3. washThe organic phase was washed with saturated sodium hydrogen carbonate solution, water and brine
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. customThe crude product was purified by silica column chromatography (ethyl acetate:hexane gradient 1:6→1:2)

Sources & evidence

ORD record
ord-dfb2d1db18e4423b9759d2e4c22765ae
Source dataset
uspto-grants-2010_09
Patent number
US07803960B2

Reaction notes

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