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

HRID 72111ノート

反応式

HRID 72111 の反応式
[Cl:1][C:2]1[C:3]([OH:14])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2.C([O-])([O-])=O.[Cs+].[Cs+].BrC1C=CC(S(O[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:14][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)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 565904841-(tert-Butyl) 2-methyl (2S,4S)-4-(((4-bromophenyl)sulfonyl)oxy)pyrrolidine-1,2-dicarboxylate2 回HCID 178487951HCID 178487951、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
50 °C

実験手順

A solution (0.35M) of the product of step 2 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 hours, 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 hours, 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)+

後処理

  1. stirringAfter stirring for 2 hours
  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)

出典と根拠

ORDレコード
ord-c30a39afcb92439caa9625789b7fa718
出典データセット
uspto-grants-2014_09
特許番号
US08828930B2

反応ノート

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