Dimethyl Sulfoxide → 1-[1-(Tert-butoxycarbonyl)-4-piperidylmethyl]-4-[4-formylbenzenesulfonyl]-2-piperazinone

HRID 1840597ノート

反応式

HRID 1840597 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][N:25]2[CH2:30][CH2:29][N:28]([S:31]([C:34]3[CH:39]=[CH:38][C:37]([CH2:40][OH:41])=[CH:36][CH:35]=3)(=[O:33])=[O:32])[CH2:27][C:26]2=[O:42])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[C:11]([O:15][C:16]([N:18]1[CH2:19][CH2:20][CH:21]([CH2:24][N:25]2[CH2:30][CH2:29][N:28]([S:31]([C:34]3[CH:35]=[CH:36][C:37]([CH:40]=[O:41])=[CH:38][CH:39]=3)(=[O:32])=[O:33])[CH2:27][C:26]2=[O:42])[CH2:22][CH2:23]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 177986031-[1-(Tert-butoxycarbonyl)-4-piperidylmethyl]-4-[4-(hydroxymethyl)benzenesulfonyl]-2-piperazinone

生成物 1

HCID 177986001-[1-(Tert-butoxycarbonyl)-4-piperidylmethyl]-4-[4-formylbenzenesulfonyl]-2-piperazinone収率 108.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒4 回

反応条件

温度
-65 °C

実験手順

To a solution of oxalyl chloride (0.70 ml) in dichloromethane (60 ml) was added dropwise at −70° C. a solution of dimethylsulfoxide (0.85 ml) in dichloromethane (10 ml). Ten minutes later, to the mixture was added dropwise a solution of 1-[1-(tert-butoxycarbonyl)-4-piperidylmethyl]-4-[4-(hydroxymethyl)benzenesulfonyl]-2-piperazinone (1.87 g) in dichloromethane (20 ml), and the mixture was stirred at about −65° C. for 1 hour. To the mixture was added triethylamine (2.79 ml), and the mixture was stirred at −60° C. to −30° C. for 2 hours. The reaction solution was diluted with dichloromethane, washed with water and saturated brine, dried and concentrated, and the the residue was purified with silica gel column chromatography (ethyl acetate). Precipitated crystals were washed with ether to give colorless crystals of 1-[1-(tert-butoxycarbonyl)-4-piperidylmethyl]-4-[4-formylbenzenesulfonyl]-2-piperazinone (2.02 g).

後処理

  1. stirringthe mixture was stirred at −60° C. to −30° C. for 2 hours
  2. washwashed with water and saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customthe the residue was purified with silica gel column chromatography (ethyl acetate)
  6. customPrecipitated crystals
  7. washwere washed with ether

出典と根拠

ORDレコード
ord-830dcc3187b54850900238c5224471f3
出典データセット
uspto-grants-2004_01
特許番号
US06680312B2

反応ノート

読み込み中…