Potassium Carbonate → Ethyl 4-((tert-butoxycarbonyl)amino)-2-(2-(3-(cyclopropylamino)-6-fluoro-2-methylquinoxalin-5-yl)-2-oxoethyl)-3-oxopentanoate

HRID 1056137노트

반응식

HRID 1056137 반응식
Br[CH2:2][C:3]([C:5]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]2[C:6]=1[N:7]=[C:8]([NH:17][CH:18]1[CH2:20][CH2:19]1)[C:9]([CH3:16])=[N:10]2)=[O:4].[C:21]([O:25][C:26]([NH:28][C@H:29]([CH3:38])[C:30](=[O:37])[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:27])([CH3:24])([CH3:23])[CH3:22].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C([O-])(O)=O.[Na+].C(Cl)(Cl)Cl>[C:21]([O:25][C:26]([NH:28][CH:29]([CH3:38])[C:30](=[O:37])[CH:31]([CH2:2][C:3]([C:5]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]2[C:6]=1[N:7]=[C:8]([NH:17][CH:18]1[CH2:20][CH2:19]1)[C:9]([CH3:16])=[N:10]2)=[O:4])[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:27])([CH3:23])([CH3:24])[CH3:22]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 11288402Ethyl (4R)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-oxopentanoateHCID 897821632-Bromo-1-(3-(cyclopropylamino)-6-fluoro-2-methylquinoxalin-5-yl)ethanone

생성물 1

HCID 89781885Ethyl 4-((tert-butoxycarbonyl)amino)-2-(2-(3-(cyclopropylamino)-6-fluoro-2-methylquinoxalin-5-yl)-2-oxoethyl)-3-oxopentanoate수율 98%

시약·촉매·용매 3

HCID 6212Chloroform용매HCID 6228Dimethylformamide용매HCID 516892Sodium Bicarbonate용매

실험 절차

A mixture of 2-bromo-1-(3-(cyclopropylamino)-6-fluoro-2-methylquinoxalin-5-yl)ethanone (293c) (0.81 g, 2.38 mmol) and (R)-ethyl 4-((tert-butoxycarbonyl)amino)-3-oxopentanoate (602) (0.74 g, 2.86 mmol) was dissolved in DMF (7.00 mL). Then K2CO3 (Acros Organics, New Jersey) (0.82 g, 5.95 mmol) was added into the reaction mixture. The overall mixture was stirred under inert atmosphere overnight. The mixture was diluted with saturated NaHCO3 (10 mL) and CHCl3 (20 mL). The layers were separated and the aq. layer was extracted with CHCl3 (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by chromatography through an Interchim PuriFlash UP (25 micron) pre-packed silica-gel column (40 gram), eluting with a gradient of 0-30% EtOAc in DCM, to provide ethyl 4-((tert-butoxycarbonyl)amino)-2-(2-(3-(cyclopropylamino)-6-fluoro-2-methylquinoxalin-5-yl)-2-oxoethyl)-3-oxopentanoate (1.20 g, 2.32 mmol, 98% yield) as a yellow oil.

후처리

  1. customThe layers were separated
  2. extractionthe aq. layer was extracted with CHCl3 (3×)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by chromatography through an Interchim PuriFlash UP (25 micron) pre-packed silica-gel column (40 gram)
  7. washeluting with a gradient of 0-30% EtOAc in DCM

출처 및 근거

ORD 기록
ord-000e2558689f4c70ae5a1e58919705f7
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394297B2

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