Pyridine → Ammonia dichloromethane

HRID 1150

반응식

HRID 1150 반응식
[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

참가 물질

9

반응물 5

HCID 1049PyridineHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 178418316HCID 178418316, 화합물HCID 178418337HCID 178418337, 화합물

생성물 2

HCID 22731429Ammonia dichloromethaneHCID 178418337HCID 178418337, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8058Hexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-48ed68423d4a4e7fb6e576167938191c
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723592

연결된 노트

불러오는 중…