Potassium Carbonate → HCID 66738591、化合物

HRID 557703ノート

反応式

HRID 557703 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]([O:15][C:16]([N:18]1[CH2:22][CH2:21][C@H:20]([NH2:23])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:11]([O:15][C:16]([N:18]1[CH2:22][CH2:21][C@H:20]([NH:23][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate2 回

生成物 1

HCID 66738591HCID 66738591、化合物収率 78.8%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 2-chloro-5-nitro-pyridine (3.4 g, 0.021 mol), (S)-(−)-3-amino-pyrrolidine-1-carboxylic acid tert-butyl ester (4 g, 0.021 mol), and potassium carbonate (14.5 g, 0.105 mol) in acetonitrile (50 mL) was heated at reflux for 24 h. The reaction was monitored by LCMS and additional (S)-(−)-3-amino-pyrrolidine-1-carboxylic acid tert-butyl ester was added until the reaction was driven to completion. The reaction mixture was then filtered and concentrated to give (S)-3-(5-nitro-pyridin-2-ylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester (5.1 g, 78.6%) as a yellow solid. LCMS calcd for C14H20N4O4 (m/e) 308, obsd 307.1(M−H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. additionwas added until the reaction
  4. filtrationThe reaction mixture was then filtered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-fbb099f33ce6455195e89bf966134a88
出典データセット
uspto-grants-2011_11
特許番号
US08058299B2

反応ノート

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