Triethylamine → HCID 59191257, compound

HRID 626046Notes

Reaction equation

HRID 626046 reaction equation
[CH2:1]([O:8][C:9]1[CH:30]=[C:29]([CH2:31][CH3:32])[CH:28]=[CH:27][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:22][CH:21]([CH2:23][OH:24])[O:20][C:19]2=[O:25])=[CH:14][C:13]=1[F:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>ClCCl.O>[CH2:1]([O:8][C:9]1[CH:30]=[C:29]([CH2:31][CH3:32])[CH:28]=[CH:27][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:22][CH:21]([CH2:23][O:24][S:41]([CH3:40])(=[O:43])=[O:42])[O:20][C:19]2=[O:25])=[CH:14][C:13]=1[F:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59191355HCID 59191355, compound

Product 1

HCID 59191257HCID 59191257, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 3-[4-(2-Benzyloxy-4-ethylphenoxy)-3-fluoro phenyl]-5-hydroxymethyloxazolidin-2-one (240 mg, 0.54 mmol) in 5 ml of dry dichloromethane and 0.16 ml (1.1 mmol) of triethylamine, cooled to 0° C., was added a solution of methanesulfonyl chloride (0.06 ml, 0.76 mmol) in 0.5 ml of dichloromethane dropwise. The reaction was allowed to warm to rt overnight. The reaction mixture was diluted with 20 ml water, 20 ml of dichloromethane were added and the layers separated. The aqueous layer was extracted with dichloromethane and the combined dichloromethane fraction was dried over anhydrous Na2SO4 and concentrated. The crude residue obtained was column purified over silica gel using 20% ethyl acetate in petroleum ether as eluant to get 120 mg, 42.8% of the title compound.

Workup

  1. additionwere added
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. dry with materialthe combined dichloromethane fraction was dried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe crude residue obtained
  7. custompurified over silica gel using 20% ethyl acetate in petroleum ether as eluant

Sources & evidence

ORD record
ord-593b18e9d24b46fb87bc35b36d501653
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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