(S)-3-(tert-butyldimethylsilanyloxy)-1-(2-fluorophenyl)propylamine → 5-(3-bromophenyl)-N-[(1S)-3-[tert-butyl(dimethyl)silyl]oxy-1-(2-fluorophenyl)propyl]-5,6,6-trimethyl-4,4-dioxo-1,4,3-oxathiazin-2-amine

HRID 339874

反応式

HRID 339874 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:20])[C:13]([CH3:15])([CH3:14])[O:12][C:11](OC)=[N:10][S:9]2(=[O:19])=[O:18])[CH:5]=[CH:6][CH:7]=1.[Si:21]([O:28][CH2:29][CH2:30][C@H:31]([NH2:39])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[F:38])([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:20])[C:13]([CH3:15])([CH3:14])[O:12][C:11]([NH:39][C@H:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[F:38])[CH2:30][CH2:29][O:28][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:22])[CH3:23])=[N:10][S:9]2(=[O:19])=[O:18])[CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 68292582(S)-3-(tert-butyldimethylsilanyloxy)-1-(2-fluorophenyl)propylamineHCID 683591715-(3-Bromophenyl)-2-methoxy-5,6,6-trimethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

生成物 1

HCID 1784316875-(3-bromophenyl)-N-[(1S)-3-[tert-butyl(dimethyl)silyl]oxy-1-(2-fluorophenyl)propyl]-5,6,6-trimethyl-4,4-dioxo-1,4,3-oxathiazin-2-amine収率 64.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 188 mg of 5-(3-bromophenyl)-2-methoxy-5,6,6-trimethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide and 157 mg of (S)-3-(tert-butyldimethylsilanyloxy)-1-(2-fluorophenyl)propylamine in 2 ml of methylene chloride was stirred at room temperature for 3 hours and the conversion was checked by LCMS. Since no reaction had taken place yet, the solvent was concentrated by rotary evaporation and the residue with addition of 0.25 ml of methylene chloride was stirred at room temperature for 17 hours. Subsequently, the reaction mixture was stirred at 50° C. for 4 hours. The crude product was purified by means of normal phase chromatography using a Flashmaster with an n-heptane/ethyl acetate gradient. The product-containing fractions were combined and concentrated by rotary evaporation. This gave the product (206 mg) with a molecular weight of 613.7 g/mol (C27H38BrFN2O4SSi); MS (ESI): m/e=614 (M+H+).

後処理

  1. concentrationthe solvent was concentrated by rotary evaporation
  2. additionthe residue with addition of 0.25 ml of methylene chloride
  3. stirringSubsequently, the reaction mixture was stirred at 50° C. for 4 hours
  4. customThe crude product was purified by means of normal phase chromatography
  5. concentrationconcentrated by rotary evaporation

出典と根拠

ORDレコード
ord-a422ca920e3840609b821f72f596c5b8
出典データセット
uspto-grants-2014_11
特許番号
US08895547B2

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