Chloride → 2-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl]-2-oxoacetic acid ethyl ester

HRID 344698ノート

反応式

HRID 344698 の反応式
CS(C)=O.[Cl-].[CH2:6]([N:13]([CH3:30])[C:14]([CH2:16][CH2:17][C:18]([N:20]1[CH2:24][CH2:23][CH2:22][C@H:21]1[CH:25]([OH:29])[C:26]([OH:28])=[O:27])=[O:19])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:31](N(CC)CC)[CH3:32]>C(Cl)Cl.O>[CH2:31]([O:27][C:26](=[O:28])[C:25]([C@@H:21]1[CH2:22][CH2:23][CH2:24][N:20]1[C:18](=[O:19])[CH2:17][CH2:16][C:14](=[O:15])[N:13]([CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:30])=[O:29])[CH3:32]

参加物

7

反応物 4

HCID 312ChlorideHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 15660980HCID 15660980、化合物

生成物 1

HCID 156609222-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl]-2-oxoacetic acid ethyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

DMSO (443 μl) was added dropwise to a solution of oxyalyl chloride (260 μl) in methylene chloride (10 ml) cooled to -78° C. The solution was stirred for 15 mins at the same temperature. A solution of (2RS)-2-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl]propanoyl]pyrrolidin-2-yl]-2-hydroxyacetic acid theyl ester (700 mg) in methylene chloride (6 ml) was added dropwise to the solution at the same temperature. The mixture was stirred for 20 mins. Triethylamine (1.42 ml) was added dropwise to the solution. The solution was stirred for 10 mins at the same temperature, and for 30 mins. at 0° C. Water was added to the reaction solution. The mixture was extracted with EtOAc. The extract was washed, dried and evaporated. The residue was purified by column chromatography on silica gel (hexane-EtOAc) to give the title compound (627 mg) having the following physical data:

後処理

  1. stirringThe mixture was stirred for 20 mins
  2. stirringThe solution was stirred for 10 mins at the same temperature
  3. waitfor 30 mins
  4. customat 0° C
  5. extractionThe mixture was extracted with EtOAc
  6. washThe extract was washed
  7. customdried
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel (hexane-EtOAc)

出典と根拠

ORDレコード
ord-8e2755fc563049288c08e13571093389
出典データセット
uspto-grants-1991_10
特許番号
US05053414

反応ノート

読み込み中…