Benzyl succinimido carbonate → HCID 10199023, compound

HRID 467523Notes

Reaction equation

HRID 467523 reaction equation
Cl.Cl.[N:3]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:7][C:6]=2[NH:5][CH:4]=1.C([O-])(O)=O.[Na+].[CH2:17]([O:24][C:25](ON1C(=O)CCC1=O)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOC(C)=O.CO>[N:3]1[C:11]2[CH2:10][CH2:9][N:8]([C:25]([O:24][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:26])[CH2:7][C:6]=2[NH:5][CH:4]=1

Participants

5

Reactant 3

HCID 83172Benzyl succinimido carbonateHCID 516892Sodium BicarbonateHCID 164180044,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine--hydrogen chloride (1/2)

Product 1

HCID 10199023HCID 10199023, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of 2.0 g of 4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride, 2.36 g of NaHCO3 and 2.45 g of N-(benzyloxycarbonyloxy)succinimide in 80 ml of dioxane/water mixture (50/50; v/v) is stirred for 16 hours at RT. The reaction mixture is extracted with EtOAc, the organic phase is washed with a saturated solution of NaHCO3, with a 0.1 M solution of HCl, with saturated NaCl solution, it is dried over Na2SO4 and the solvent is evaporated under vacuum. The residue is purified by silica gel chromatography, eluting with DCM/MeOH mixture. 1.9 g of the expected compound is obtained.

Workup

  1. extractionThe reaction mixture is extracted with EtOAc
  2. washthe organic phase is washed with a saturated solution of NaHCO3, with a 0.1 M solution of HCl, with saturated NaCl solution, it
  3. dry with materialis dried over Na2SO4
  4. customthe solvent is evaporated under vacuum
  5. customThe residue is purified by silica gel chromatography
  6. washeluting with DCM/MeOH mixture

Sources & evidence

ORD record
ord-7ee478b84c364cc2b7a5c7ef3b336de1
Source dataset
uspto-grants-2014_01
Patent number
US08623862B2

Reaction notes

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