1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1''-{(2S)-3-[(6-Chloronaphthalen-2-yl)sulfonyl]-2-hydroxypropanoyl}-1,4''-bipiperidin-2-one

HRID 20214ノート

反応式

HRID 20214 の反応式
CCN=C=NCCCN(C)C.[Cl:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([S:23]([CH2:26][C@@H:27]([OH:31])[C:28]([OH:30])=O)(=[O:25])=[O:24])[CH:17]=[CH:16]2.[N:32]1([CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH2:37][CH2:36][CH2:35][CH2:34][C:33]1=[O:38].C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[Cl:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([S:23]([CH2:26][C@@H:27]([OH:31])[C:28]([N:42]1[CH2:41][CH2:40][CH:39]([N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][C:33]3=[O:38])[CH2:44][CH2:43]1)=[O:30])(=[O:24])=[O:25])[CH:17]=[CH:16]2

参加物

6

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 21839852[1,4'-Bipiperidin]-2-oneHCID 66854329(2S)-3-[(6-chloro-2-naphthyl)sulfonyl]-2-hydroxypropionic acid

生成物 1

HCID 115838001''-{(2S)-3-[(6-Chloronaphthalen-2-yl)sulfonyl]-2-hydroxypropanoyl}-1,4''-bipiperidin-2-one収率 55.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

WSC (0.19 g) was added to a mixture of (2S)-3-[(6-chloronaphthalen-2-yl)sulfonyl]-2-hydroxypropionic acid (0.31 g), 1,4′-bipiperidin-2-one (0.18 g) and HOBt (0.15 g) in DMF (15 mL) and the mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure, and diluted with dichloromethane and an aqueous sodium bicarbonate solution. The organic layer was separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=10/1) to obtain the title compound (0.26 g, 54%) as a colorless powder.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=10/1)

出典と根拠

ORDレコード
ord-c5f16dba08814d3e8444b69460007b9d
出典データセット
uspto-grants-2010_06
特許番号
US07745623B2

反応ノート

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