Pyridine → Ammonia dichloromethane

HRID 1003924Notes

Reaction equation

HRID 1003924 reaction equation
[NH2:1][C@H:2](CO)CC1N=CNC=1.[H-].[Na+].[ClH:13].[ClH:14].C[NH:16][C@H:17]([CH2:24][OH:25])[CH2:18][C:19]1[N:23]=[CH:22][NH:21][CH:20]=1.N1C=CC=CC=1>CCCCCC.CN(C=O)C>[NH3:1].[CH2:2]([Cl:14])[Cl:13].[NH2:16][C@H:17]([CH2:24][OH:25])[CH2:18][C:19]1[N:23]=[CH:22][NH:21][CH:20]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 24758Sodium hydrideHCID 178418337HCID 178418337, compoundHCID 178484888HCID 178484888, 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 3× with hexane, under argon, in 3.0 mL DMF was added in portions 500 mg (2.3 mmol) of N-methylhistidinol 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 TBDMSC1 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-263e2b32bca64b08bf275a1181b01497
Source dataset
uspto-grants-2000_04
Patent number
US06048698

Reaction notes

Loading…