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

HRID 2186185노트

반응식

HRID 2186185 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매4회

반응 조건

온도
-65 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-72d2c5ba6fe64161979573338f2a9719
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06403595B1

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