Dimethyl Sulfoxide → 4'-[3-(3-Oxo-1-pyrrolidinyl)propoxy][1,1'-biphenyl]-4-carbonitrile

HRID 1057780ノート

反応式

HRID 1057780 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][C@@H:12]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=3)=[CH:23][CH:22]=2)[CH2:13]1.C(N(CC)CC)C>C(Cl)Cl>[O:11]=[C:12]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:28]=[CH:29][C:30]([C:33]#[N:34])=[CH:31][CH:32]=3)=[CH:23][CH:22]=2)[CH2:13]1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 98802084'-{3-[(3R)-3-hydroxypyrrolidinyl]propoxy}[1,1'-biphenyl]-4-carbonitrile

生成物 1

HCID 99230964'-[3-(3-Oxo-1-pyrrolidinyl)propoxy][1,1'-biphenyl]-4-carbonitrile収率 60%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Oxalyl chloride (0.195 mmol) in dry CH2Cl2 (5 mL) under an atmosphere of nitrogen at −78° C. was treated with DMSO (0.39 mmol). After 15 minutes of stirring, the product from Example 153 was added and the mixture was stirred for another 15 minutes. Triethylamine (0.45 mmol) was added and the mixture was gradually allowed to warm to 0° C. The solution was partitioned between water (50 mL) and dichloromethane (50 mL). The organic layer was washed with brine (50 mL), dried over sodium sulfate and filtered. The filtrate was evaporated under reduced pressure and the residue purified by chromatography (CHCl3:MeOH:NH4OH, 9:1:0.1) to provide the title compound (60% yield).

後処理

  1. stirringthe mixture was stirred for another 15 minutes
  2. customThe solution was partitioned between water (50 mL) and dichloromethane (50 mL)
  3. washThe organic layer was washed with brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. customthe residue purified by chromatography (CHCl3:MeOH:NH4OH, 9:1:0.1)

出典と根拠

ORDレコード
ord-e8ea387411d24c6b9bc3c922023d97be
出典データセット
uspto-grants-2003_02
特許番号
US06515013B2

反応ノート

読み込み中…