Dimethyl Sulfoxide → 4-[(1R,7aS)-1-Methyl-3,7-dioxo-hexahydropyrrolo[1,2-c]imidazol-2-yl]-2-chloro-3-methylbenzonitrile

HRID 751137ノート

反応式

HRID 751137 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][C@@H:12]1[C@@H:19]2[N:15]([C:16](=[O:31])[N:17]([C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([Cl:29])[C:22]=3[CH3:30])[C@H:18]2[CH3:20])[CH2:14][CH2:13]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:20][C@H:18]1[N:17]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([Cl:29])[C:22]=2[CH3:30])[C:16](=[O:31])[N:15]2[CH2:14][CH2:13][C:12](=[O:11])[C@H:19]12

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 167337664-[(1S,7S,7aR)-7-Hydroxy-1-methyl-3-oxo-hexahydropyrrolo[1,2-c]imidazol-2-yl]-2-chloro-3-methylbenzonitrile

生成物 1

HCID 684556054-[(1R,7aS)-1-Methyl-3,7-dioxo-hexahydropyrrolo[1,2-c]imidazol-2-yl]-2-chloro-3-methylbenzonitrile

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of DMSO (20 μL) in CH2Cl2 (1 mL) at −78° C. was added oxalyl chloride (1.0 M in CH2Cl2, 131 μL). This mixture was stirred at −78° C. for 30 min. and then a solution of 61K in CH2Cl2 (20 mg in 1 mL). The reaction was stirred at −78° C. for 1 h and then i-Pr2NEt (100 μL) was added and the reaction was allowed to warm to rt over 1 h. The reaction was extracted with EtOAc and washed twice with 1N HCl and once with saturated NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated. Purification by flash chromatography (silica gel, 40% EtOAc/CH2Cl2) provided the title compound (18 mg): MS (ES) m/z 304.42 [M+H]+

後処理

  1. stirringThe reaction was stirred at −78° C. for 1 h
  2. temperatureto warm to rt over 1 h
  3. extractionThe reaction was extracted with EtOAc
  4. washwashed twice with 1N HCl and once with saturated NaHCO3
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash chromatography (silica gel, 40% EtOAc/CH2Cl2)

出典と根拠

ORDレコード
ord-6990011de6cc4b63afdfcda68ef903e1
出典データセット
uspto-grants-2008_07
特許番号
US07405234B2

反応ノート

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