Hydrochloric Acid → HCID 4101679, compound

HRID 377697Notes

Reaction equation

HRID 377697 reaction equation
[C:1]([NH:4][CH2:5][C:6]([OH:8])=O)(=[O:3])[CH3:2].Cl.N[CH2:11][C:12]([NH2:14])=[O:13].C([N:17](CC)CC)C.Cl>O.C(#N)C.O>[C:12]([NH:14][CH2:2][C:1]([NH:4][CH2:5][C:6]([NH2:17])=[O:8])=[O:3])(=[O:13])[CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471Triethylamine2×HCID 10972AcetylglycineHCID 2723639Glycinamide hydrochloride

Product 1

HCID 4101679HCID 4101679, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

N-Acetylglycine (5 g, 43 mmole) and 9.5 g (86 mmole) of glycinamide hydrochloride were dissolved in a 150 mL of a mixture of water-acetonitrile (50:50), 8.65 g (86 mmole) of triethylamine (TEA) and 12.6 g (64 mmole) of 1-ethyl-3(3-dimethyl aminopropyl)carbodiimide (EDC) as a coupling reagent were added to the mixture and the mixture was refluxed for 12 hours. The mixture was left to cool at room temperature, the insoluble materials were filtered and the filtrate was evaporated to dryness in vacuum. The residue was recrystallized from a big fraction of acetonitrile to get a mixture of the product with the salt TEA:HCl, the solid crystals were dissolved in distilled water and purified from the salt by a strong cation exchange chromatography (120 plus). The water fractions were collected and the water was removed by lyophilization to get a pure product 4.5 g (26 mmole), yield of 60%.

Workup

  1. additionwere added to the mixture
  2. temperaturethe mixture was refluxed for 12 hours
  3. waitThe mixture was left
  4. filtrationthe insoluble materials were filtered
  5. customthe filtrate was evaporated to dryness in vacuum
  6. customThe residue was recrystallized from a big fraction of acetonitrile
  7. customto get
  8. custompurified from the salt by a strong cation exchange chromatography (120 plus)
  9. customThe water fractions were collected
  10. customthe water was removed by lyophilization

Sources & evidence

ORD record
ord-f354761be1ba4dce898223dc130cd73c
Source dataset
uspto-grants-2000_02
Patent number
US06028102

Reaction notes

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