Benzyl succinimido carbonate → HCID 178525108, compound

HRID 467518Notes

Reaction equation

HRID 467518 reaction equation
Cl.Cl.[NH:3]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:7][C:6]=2[N: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>[NH: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[N: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 178525108HCID 178525108, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of 2.0 g of 4,5,6,7-tetrahydro-1H-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 0.1M HCl solution, with saturated NaCl solution, it is dried and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, 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 0.1M HCl solution, with saturated NaCl solution, it
  3. customis dried
  4. customthe solvent is evaporated under vacuum
  5. customThe residue is chromatographed on silica gel
  6. washeluting with DCM/MeOH mixture

Sources & evidence

ORD record
ord-c5f2c5d2bbad4e7ab57933ee0fe0f120
Source dataset
uspto-grants-2014_01
Patent number
US08623862B2

Reaction notes

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