Triethylamine → HCID 58869139, compound

HRID 2355218Notes

Reaction equation

HRID 2355218 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][CH:17]([CH2:21][OH:22])[O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].C(N(CC)CC)C>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][O:22][S:24]([CH3:23])(=[O:26])=[O:25])[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 66917441HCID 66917441, compound

Product 1

HCID 58869139HCID 58869139, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of [7-(3-fluoro-benzenesulfonyl)-chroman-2-yl]-methanol (10.0 g, 0.032 mol) in 200 mL of methylene chloride at −10° C. was added methanesulfonyl chloride (2.76 mL, 0.036 mol) and triethylamine (4.95 mL, 0.036 mol). The reaction mixture was stirred for one hour at −10° C. and was then quenched by addition of 10% aqueous NaHCO3. The organic layer was separated, washed with water and brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (hexanes:EtOAc 85:15) to give 11.35 g (92%) of methanesulfonic acid (R)-7-(3-fluoro-benzenesulfonyl)-chroman-2-ylmethyl ester.

Workup

  1. customwas then quenched by addition of 10% aqueous NaHCO3
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (hexanes:EtOAc 85:15)

Sources & evidence

ORD record
ord-ebf469a6226b46d5946e3a75135004ea
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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