Pyridine → Ammonia dichloromethane

HRID 1150

反応式

HRID 1150 の反応式
[NH2:1][C@H:2](CO)CC1N=CNC=1.[H-].[Na+].[ClH:13].[ClH:14].[NH2:15][C@H:16]([CH2:23][OH:24])[CH2:17][C:18]1[N:22]=[CH:21][NH:20][CH:19]=1.N1C=CC=CC=1.CC([Si](Cl)(C)C)(C)C>CCCCCC.CN(C=O)C>[NH3:1].[CH2:2]([Cl:14])[Cl:13].[NH2:15][C@H:16]([CH2:23][OH:24])[CH2:17][C:18]1[N:22]=[CH:21][NH:20][CH:19]=1

参加物

9

反応物 5

HCID 1049PyridineHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 178418316HCID 178418316、化合物HCID 178418337HCID 178418337、化合物

生成物 2

HCID 22731429Ammonia dichloromethaneHCID 178418337HCID 178418337、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒

実験手順

TBDMS protected histidinol 14--To a stirred solution of 205 mg (5.1 mmol) of NaH washed 3× with hexane, under argon, in 3.0 mL DMF was added in portions 500 mg (2.3 mmol) of histidinol dihydrochloride, resulting in moderate gas evolution. The solution was stirred for 1.5 h, then 1.8 mL (23 mmol) of anhydrous pyridine and 693.0 mg (4.6 mmol) of TBDMSCl was added. The solution was stirred for 1.5 h, concentrated in vacuo and flash chromatographed on silica with 15% CH3OH.NH3 /CH2Cl2 to yield 14.

後処理

  1. customresulting in moderate gas evolution
  2. stirringThe solution was stirred for 1.5 h
  3. concentrationconcentrated in vacuo and flash
  4. customchromatographed on silica with 15% CH3OH

出典と根拠

ORDレコード
ord-48ed68423d4a4e7fb6e576167938191c
出典データセット
uspto-grants-1998_03
特許番号
US05723592

関連ノート

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