Trifluoroacetic acid → Biphenyl-4-yl-(3-hydroxyoxetan-3-yl)methanesulfonamide

HRID 339895

반응식

HRID 339895 반응식
[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][C:4]([CH2:7][S:8]([NH:11]CC2C=CC(OC)=CC=2OC)(=[O:10])=[O:9])=[CH:3][CH:2]=1.C([Li])CCC.[O:34]1[CH2:37][C:36](=[O:38])[CH2:35]1.FC(F)(F)C(O)=O>C1COCC1.CCCCCC>[C:1]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:2]=[CH:3][C:4]([CH:7]([C:36]2([OH:38])[CH2:37][O:34][CH2:35]2)[S:8]([NH2:11])(=[O:9])=[O:10])=[CH:5][CH:6]=1

참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 150242543-OxetanoneHCID 68291406C-biphenyl-4-yl-N-(2,4-dimethoxybenzyl)methanesulfonamideHCID 178418339Butyllithium

생성물 1

HCID 68359244Biphenyl-4-yl-(3-hydroxyoxetan-3-yl)methanesulfonamide

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

Under inert gas, 0.500 g of C-biphenyl-4-yl-N-(2,4-dimethoxybenzyl)methanesulfonamide was initially charged in 5 ml of THF and then, at −78° C., 1.8 ml of a 1.6 N butyllithium solution in hexane were added dropwise. The reaction mixture was stirred for 5 minutes and then admixed dropwise with 0.24 ml of 3-oxetanone. The mixture was stirred at constant temperature for 5 minutes, 0.28 ml of trifluoroacetic acid were added and the mixture was allowed to come to room temperature. The solvent was removed under reduced pressure. The residue was dissolved in 2 ml of dichloromethane, and 2 ml of trifluoroacetic acid were added. After stirring at room temperature for 60 minutes, 50 ml of saturated potassium carbonate solution were added and the mixture was extracted with dichloromethane, dried over magnesium sulfate and concentrated. The crude product was purified by means of normal phase chromatography using a Flashmaster with an n-heptane/ethyl acetate gradient. This gave the product (170 mg) with a molecular weight of 319.4 g/mol (C16H17NO4S).

후처리

  1. stirringThe mixture was stirred at constant temperature for 5 minutes
  2. customto come to room temperature
  3. customThe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in 2 ml of dichloromethane
  5. addition2 ml of trifluoroacetic acid were added
  6. stirringAfter stirring at room temperature for 60 minutes
  7. addition50 ml of saturated potassium carbonate solution were added
  8. extractionthe mixture was extracted with dichloromethane
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. customThe crude product was purified by means of normal phase chromatography

출처 및 근거

ORD 기록
ord-8878873f434541c9a678482db6dc0627
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895547B2

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