Phenethylamine → (S)-2-Oxo-5-phenethylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester

HRID 1668419ノート

反応式

HRID 1668419 の反応式
[CH2:1]([O:8][C:9]([N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C@H:12]1[C:17]([OH:19])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.[CH2:31]([NH2:39])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClCCl.CN(C1C=CN=CC=1)C>[CH2:1]([O:8][C:9]([N:11]1[C@H:12]([C:17](=[O:19])[NH:39][CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:13][CH2:14][C:15]1=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 1001PhenethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 6376481-(Phenylmethyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylate

生成物 1

HCID 57612752(S)-2-Oxo-5-phenethylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

反応条件

温度
2.5 °C

実験手順

(S)-5-Oxo-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (14.9 g, 57 mmol) is suspended in dichloromethane (100 mL) and added DMAP (7.1 g, 58 mmol) while cooling on ice (0-5° C.). The suspension immediately clarified. EDCI (11.1 g, 58 mmol) is added resulting in precipitation which quickly clarified again. Phenethylamine (6.8 mL, 54 mmol) is added slowly via syringe. The reaction is complete in one half hour. The dichloromethane layer is washed with aqueous 10% citric acid, water and saturated bicarb, then dried over anhydrous sodium sulfate, filtered and concentrated to a white solid. LCMS characterization ES+367.1 (m+1).

後処理

  1. customresulting in precipitation which
  2. waitThe reaction is complete in one half hour
  3. washThe dichloromethane layer is washed with aqueous 10% citric acid, water and saturated bicarb
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a white solid

出典と根拠

ORDレコード
ord-4f1e8a73cb34449180ba72306e66a5ab
出典データセット
uspto-grants-2011_08
特許番号
US07989441B2

反応ノート

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