Ethyl 7-(3-phenyl-2-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate → 7-(3-Phenyl-2-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

HRID 406188ノート

反応式

HRID 406188 の反応式
[C:1]1([C:7]2[N:12]=[C:11]3[N:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25]CC)=[O:24])[CH2:14][CH2:15][CH2:16][C:10]3=[N:9][C:8]=2[C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1COCC1.O>[C:1]1([C:7]2[N:12]=[C:11]3[N:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[CH2:14][CH2:15][CH2:16][C:10]3=[N:9][C:8]=2[C:28]2[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

4

反応物 1

HCID 66666309Ethyl 7-(3-phenyl-2-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

生成物 1

HCID 566442737-(3-Phenyl-2-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Ethyl 7-(3-phenyl-2-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate (158 mg, 0.345 mmol) in THF (4 ml) and water (1 ml) at RT was treated with LiOH monohydrate (43.5 mg, 1.036 mmol) and stirred at RT for 16 hours. The organic solvent was removed in vacuo and the residue was diluted with water (20 ml). The pH was adjusted to pH4 with aqueous 10% citric acid solution. The mixture was extracted with DCM (×3) and the organic extracts were passed through a phase separating column and concentrated in vacuo. The resulting crude product was purified by chromatography on silica eluting with 0-40% EtOAc/iso-hexane followed by chiral separation using Supercritical Fluid Chromatography to afford the title compound;

後処理

  1. customThe organic solvent was removed in vacuo
  2. additionthe residue was diluted with water (20 ml)
  3. extractionThe mixture was extracted with DCM (×3)
  4. customseparating column
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude product was purified by chromatography on silica eluting with 0-40% EtOAc/iso-hexane
  7. customfollowed by chiral separation

出典と根拠

ORDレコード
ord-a461edcff1e342bc8b1aa5a8063520ef
出典データセット
uspto-grants-2014_06
特許番号
US08754085B2

反応ノート

読み込み中…