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 2276534노트

반응식

HRID 2276534 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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;

후처리

  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

출처 및 근거

ORD 기록
ord-c8880f655bb34a068bfa86c91f7e4dce
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09132127B2

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