Cesium carbonate → 1-(tert-Butyl) 2-methyl (2S,4R)-4-((3-chloro-7-methoxyquinoxalin-2-yl)oxy)pyrrolidine-1,2-dicarboxylate

HRID 1008853노트

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HRID 1008853 반응식
[Cl:1][C:2]1[C:3](O)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8](OC)=[CH:7][CH:6]=2.[C:15]([O-:18])([O-])=O.[Cs+].[Cs+].BrC1C=CC(S([O:31][C@@H:32]2[CH2:36][N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C@H:34]([C:44]([O:46][CH3:47])=[O:45])[CH2:33]2)(=O)=O)=CC=1>CN1C(=O)CCC1.O.CCOC(C)=O>[Cl:1][C:2]1[C:3]([O:31][C@H:32]2[CH2:36][N:35]([C:37]([O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[O:38])[C@H:34]([C:44]([O:46][CH3:47])=[O:45])[CH2:33]2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[C:7]([O:18][CH3:15])[CH:6]=2

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 565904841-(tert-Butyl) 2-methyl (2S,4S)-4-(((4-bromophenyl)sulfonyl)oxy)pyrrolidine-1,2-dicarboxylate2회HCID 178488023HCID 178488023, 화합물

생성물 1

HCID 584284571-(tert-Butyl) 2-methyl (2S,4R)-4-((3-chloro-7-methoxyquinoxalin-2-yl)oxy)pyrrolidine-1,2-dicarboxylate수율 35%

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
50 °C

실험 절차

A solution (0.35 M) of 3-chloro-6-methoxyquinoxalin-2-ol in NMP was treated with Cs2CO3 (1.5 eq) and 1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate (1.1 eq). The resulting mixture was stirred at 50° C. for 18 h, then a further portion (0.1 eq) of 1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate was added. After stirring for 2 h, the mixture was cooled and diluted with H2O and EtOAc. The organic phases were washed with aqueous HCl (1 N), saturated aqueous NaHCO3 and brine. The dried organic phase was concentrated to a residue that was purified by flash-chromatography (0-60% EtOAc/petroleum ether) to give the title compound (35% for two steps) as a solid. MS (ES+) m/z 438 (M+H)+

후처리

  1. stirringAfter stirring for 2 h
  2. temperaturethe mixture was cooled
  3. washThe organic phases were washed with aqueous HCl (1 N), saturated aqueous NaHCO3 and brine
  4. concentrationThe dried organic phase was concentrated to a residue that
  5. customwas purified by flash-chromatography (0-60% EtOAc/petroleum ether)

출처 및 근거

ORD 기록
ord-8ad8e5605e5c497cb5d72223df89e048
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973040B2

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