Tetraethyl orthocarbonate → 5-(3-Bromophenyl)-2-ethoxy-5-fluoro-6,6-dimethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

HRID 339880

反応式

HRID 339880 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([F:17])([S:13]([NH2:16])(=[O:15])=[O:14])[C:9]([OH:12])([CH3:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[CH2:18]([O:20][C:21](OCC)(OCC)OCC)[CH3:19]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([F:17])[C:9]([CH3:11])([CH3:10])[O:12][C:21]([O:20][CH2:18][CH3:19])=[N:16][S:13]2(=[O:14])=[O:15])[CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 66213Tetraethyl orthocarbonateHCID 68292393HCID 68292393、化合物

生成物 1

HCID 683592075-(3-Bromophenyl)-2-ethoxy-5-fluoro-6,6-dimethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

A mixture of 75 mg of 1-(3-bromophenyl)-1-fluoro-2-hydroxy-2-methylpropane-1-sulfonamide in 5 ml of tetraethoxymethane and 1 ml of acetic acid was stirred at 100° C. for 1.5 hours. The conversion was checked by LCMS. Since it was incomplete, the reaction mixture was stirred at 100° C. for a further 3.5 hours. After the removal of the solvents under reduced pressure, the residue 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 (45.6 mg) with a molecular weight of 380.2 g/mol (C13H15BrFNO4S).

後処理

  1. stirringthe reaction mixture was stirred at 100° C. for a further 3.5 hours
  2. customAfter the removal of the solvents under reduced pressure
  3. customthe residue was purified by means of normal phase chromatography
  4. concentrationconcentrated by rotary evaporation

出典と根拠

ORDレコード
ord-9bfd0b628c204c6d95b22f944706bc75
出典データセット
uspto-grants-2014_11
特許番号
US08895547B2

関連ノート

読み込み中…