tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate → tert-butyl(3S)-3-(hydroxymethyl)-4-[2-hydroxy-2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazine-1-carboxylate

HRID 1501926ノート

反応式

HRID 1501926 の反応式
[O:1]1[CH2:3][CH:2]1[C:4]1[CH:13]=[CH:12][C:7]2[C:8](=[O:11])[O:9][CH2:10][C:6]=2[CH:5]=1.[C:14]([N:21]1[CH2:26][CH2:25][NH:24][C@H:23]([CH2:27][OH:28])[CH2:22]1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>C(O)C>[OH:28][CH2:27][C@H:23]1[N:24]([CH2:3][CH:2]([OH:1])[C:4]2[CH:13]=[CH:12][C:7]3[C:8](=[O:11])[O:9][CH2:10][C:6]=3[CH:5]=2)[CH2:25][CH2:26][N:21]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:22]1

参加物

4

反応物 2

HCID 24820294tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 595687155-(oxiran-2-yl)-2-benzofuran-1(3H)-one

生成物 1

HCID 71271745tert-butyl(3S)-3-(hydroxymethyl)-4-[2-hydroxy-2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazine-1-carboxylate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
150 °C

実験手順

5-(Oxiran-2-yl)-2-benzofuran-1(3H)-one (1.5 g, 8.5 mmol) and commercially available (S)-4-N—BOC-2-hydroxymethyl piperazine (2.394 g, 11.07 mmol) were combined in ethanol (10 mL) in a microwave tube. The mixture was degassed then heated for 60 min at 150° C. LC-MS showed the product peak. The reaction was worked up by adding ethyl acetate and washing once with brine. The organic layer was separated, dried, and concentrated to dryness. The crude product was purified by MPLC using an 80 g Redi-sep column and eluted with 50%-100% EtOAc/hexane yielding the title compound.

後処理

  1. customThe mixture was degassed
  2. additionby adding ethyl acetate
  3. washwashing once with brine
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated to dryness
  7. customThe crude product was purified by MPLC
  8. washeluted with 50%-100% EtOAc/hexane yielding the title compound

出典と根拠

ORDレコード
ord-46dab300aa3e4aba998386750e6c0722
出典データセット
uspto-grants-2015_12
特許番号
US09206199B2

反応ノート

読み込み中…