Triethylamine → N-[(Benzyloxy)carbonyl]glycylglycinamide

HRID 377698Notes

Reaction equation

HRID 377698 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.Cl.[NH2:32][CH2:33][C:34]([NH2:36])=[O:35].C(N(CC)CC)C>ClCCl>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([NH:32][CH2:33][C:34]([NH2:36])=[O:35])=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 14349BenzyloxycarbonylglycineHCID 2723639Glycinamide hydrochloride

Product 1

HCID 297865N-[(Benzyloxy)carbonyl]glycylglycinamideYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-benzyloxycarbonylglycine (3 g, 14.4 mmole) were dissolved in 200 mL of dichloromethane and 4.5 g (21.6 mmole) of DCC were added. The mixture was stirred at room temperature for 2 hours, the insoluble materials were removed and 3.2 g (28.8 mmole) of glycinamide hydrochloride and 2.93 g (28.8 mmole) of TEA (triethylamine) were added to the filtrate. The reaction was stirred for 24 hours at room temperature, the insoluble materials were filtered and the filtrate was evaporated to dryness in vacuum. The residue was recrystallized from distilled water to get a pure product 1.9 g (7.2 mmole), yield of 50%.

Workup

  1. customthe insoluble materials were removed
  2. stirringThe reaction was stirred for 24 hours at room temperature
  3. filtrationthe insoluble materials were filtered
  4. customthe filtrate was evaporated to dryness in vacuum
  5. customThe residue was recrystallized
  6. distillationfrom distilled water

Sources & evidence

ORD record
ord-5520e2a0fd7c4403a09eeac5a8c54fd2
Source dataset
uspto-grants-2000_02
Patent number
US06028102

Reaction notes

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