Heptanoic acid, 7-oxo-, ethyl ester → rac-5-(7-Ethoxy-7-oxoheptyl)-2,3-diphenyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine-7,8-diyl diacetate

HRID 406197노트

반응식

HRID 406197 반응식
[C:1]([O:4][CH:5]1[CH2:26][NH:25][C:8]2=[N:9][C:10]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:12]=[C:7]2[CH:6]1[O:27][C:28](=[O:30])[CH3:29])(=[O:3])[CH3:2].O=[CH:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O>[C:1]([O:4][CH:5]1[CH2:26][N:25]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:8]2=[N:9][C:10]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[C:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:12]=[C:7]2[CH:6]1[O:27][C:28](=[O:30])[CH3:29])(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 77609Heptanoic acid, 7-oxo-, ethyl ester2회HCID 5049666Sodium triacetoxyborohydride2회HCID 68070482Rac-2,3-diphenyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine-7,8-diyl diacetate2회

생성물 1

HCID 123258647rac-5-(7-Ethoxy-7-oxoheptyl)-2,3-diphenyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine-7,8-diyl diacetate

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 962Water용매

실험 절차

To a solution of rac-2,3-diphenyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine-7,8-diyl diacetate (Intermediate I) (69 mg, 0.171 mmol) in DCE (3 ml) was added ethyl 7-oxoheptanoate (88 mg, 0.513 mmol) followed by sodium triacetoxyborohydride (109 mg, 0.513 mmol). The reaction was left to stir overnight at room temperature under an atmosphere of nitrogen. To the reaction mixture was added further ethyl 7-oxoheptanoate (88 mg, 0.513 mmol) followed by sodium triacetoxyborohydride (109 mg, 0.513 mmol). The reaction mixture was left to stir at RT under an atmosphere of nitrogen for 4 days. The mixture was diluted with water and extracted with EtOAc (3×20 ml). The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo. The resulting crude product was purified by chromatography on silica eluting with 0-70% EtOAc/iso-hexane to afford the title compound;

후처리

  1. waitThe reaction was left
  2. waitThe reaction mixture was left
  3. stirringto stir at RT under an atmosphere of nitrogen for 4 days
  4. extractionextracted with EtOAc (3×20 ml)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting crude product was purified by chromatography on silica eluting with 0-70% EtOAc/iso-hexane

출처 및 근거

ORD 기록
ord-53ea9981c86240eebff42d0d92968ab6
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754085B2

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