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

HRID 1056137ノート

反応式

HRID 1056137 の反応式
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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-000e2558689f4c70ae5a1e58919705f7
出典データセット
uspto-grants-2016_07
特許番号
US09394297B2

反応ノート

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