(S)-3-(tert-butyldimethylsilanyloxy)-1-(2-fluorophenyl)propylamine → HCID 178431662、化合物

HRID 339885

反応式

HRID 339885 の反応式
[Si]([O:8][CH2:9][CH2:10][C@H:11]([NH2:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])(C(C)(C)C)(C)C.[C:20]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:25]=[CH:24][C:23]([CH:26]2[C:31]([CH3:33])([CH3:32])[O:30][C:29](OCC)=[N:28][S:27]2(=[O:38])=[O:37])=[CH:22][CH:21]=1>ClCCl>[C:20]1([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:25]=[CH:24][C:23]([CH:26]2[C:31]([CH3:32])([CH3:33])[O:30][C:29]([NH:19][C@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])[CH2:10][CH2:9][OH:8])=[N:28][S:27]2(=[O:37])=[O:38])=[CH:22][CH:21]=1

参加物

4

反応物 2

HCID 68292582(S)-3-(tert-butyldimethylsilanyloxy)-1-(2-fluorophenyl)propylamineHCID 683591725-Biphenyl-4-yl-2-ethoxy-6,6-dimethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

生成物 1

HCID 178431662HCID 178431662、化合物収率 47.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In a round-bottom flask, 346 mg of 5-biphenyl-4-yl-2-ethoxy-6,6-dimethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide were dissolved under inert gas in 2 ml of dichloromethane and admixed with 328 mg of (S)-3-(tert-butyldimethylsilanyloxy)-1-(2-fluorophenyl)propylamine. After concentration by rotary evaporation, the residue was suspended in 0.5 ml of dichloromethane and stirred at room temperature for 18 hours. The conversion was checked by LCMS. Since reactant was still present, the reaction mixture, after the addition of 1 ml of toluene, was stirred at 50° C. for 1 hour. Even after stirring at 75° C. for a further 4 hours, the conversion remained incomplete. The solvent was removed under reduced pressure. To detach the protecting group, the residue was taken up in 1 ml of methanol and, after addition of 0.05 ml of concentrated hydrochloric acid, stirred at room temperature for 1 hour. After concentration by rotary evaporation, the residue was purified in a purification laboratory by means of preparative HPLC. The product-containing fractions were combined and freed of the solvent under reduced pressure. The aqueous residue was extracted with ethyl acetate, and the combined organic phases were dried using a diatomaceous earth cartridge (Varian Chem Elut®) and concentrated by rotary evaporation. The residue was dissolved in a mixture of acetonitrile and water and lyophilized. This gave the product (221 mg) with a molecular weight of 482.6 g/mol (C26H27FN2O4S); MS (ESI): m/e=483 (M+H+).

後処理

  1. concentrationAfter concentration
  2. customby rotary evaporation
  3. additionthe reaction mixture, after the addition of 1 ml of toluene
  4. stirringwas stirred at 50° C. for 1 hour
  5. stirringEven after stirring at 75° C. for a further 4 hours
  6. customThe solvent was removed under reduced pressure
  7. additionafter addition of 0.05 ml of concentrated hydrochloric acid
  8. stirringstirred at room temperature for 1 hour
  9. concentrationAfter concentration
  10. customby rotary evaporation
  11. customthe residue was purified in a purification laboratory by means of preparative HPLC
  12. extractionThe aqueous residue was extracted with ethyl acetate
  13. customthe combined organic phases were dried
  14. concentrationconcentrated by rotary evaporation
  15. dissolutionThe residue was dissolved in a mixture of acetonitrile and water

出典と根拠

ORDレコード
ord-ed828bc7b9334673b9c9e69696921922
出典データセット
uspto-grants-2014_11
特許番号
US08895547B2

関連ノート

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