Triethylamine → HCID 16225955, compound

HRID 2355225Notes

Reaction equation

HRID 2355225 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH2:15][CH2:16][C@H:17]([CH2:21][NH2:22])[O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH2:15][CH2:16][C@H:17]([CH2:21][NH:22][S:31]([CH3:30])(=[O:33])=[O:32])[O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58869130HCID 58869130, compound

Product 1

HCID 16225955HCID 16225955, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of C—[(R)-7-(3-Fluoro-benzenesulfonyl)-chroman-2-yl]-methylamine (0.28 g, 0.871 mmol) in methylene chloride (10 mL) was added triethylamine (0.363 mL, 0.26 mmol.) and methanesulfonyl chloride (0.071 g, 0.915 mmol) The mixture was stirred at room temperature for two hours, and was then quenched by addition of water. The mixture was extracted with methylene chloride, and the combined organic layers were washed with water and brine, dried (Na2SO4), filtered and concentrated under reduced pressure. Purification of the residue by flash chromatography (hexanes:EtOAc 1:1) gave 0.296 g of N-[(R)-7-(3-fluoro-benzenesulfonyl)-chroman-2-ylmethyl]-methanesulfonamide as a foam. MS (M+H)=400.

Workup

  1. customwas then quenched by addition of water
  2. extractionThe mixture was extracted with methylene chloride
  3. washthe combined organic layers were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification of the residue by flash chromatography (hexanes:EtOAc 1:1)

Sources & evidence

ORD record
ord-b9d9abe64f7f469b87d6a451e23155f3
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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