Pyridine → Ammonia dichloromethane

HRID 378201Notes

Reaction equation

HRID 378201 reaction equation
[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

Participants

9

Reactant 5

HCID 1049PyridineHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 178418316HCID 178418316, compoundHCID 178418337HCID 178418337, compound

Product 2

HCID 22731429Ammonia dichloromethaneHCID 178418337HCID 178418337, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

TBDMS protected histidinol 14--To a stirred solution of 205 mg (5.1 mmol) of NaH washed 3x 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.

Workup

  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

Sources & evidence

ORD record
ord-e0f4c8511699468c947b68512ff8c1c8
Source dataset
uspto-grants-2000_02
Patent number
US06030776

Reaction notes

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