Dicyclohexylcarbodiimide → Glycylglycinamide

HRID 377696Notes

Reaction equation

HRID 377696 reaction equation
C([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=O)(C)(C)C.Cl.[NH2:14][CH2:15]C(N)=O.C1([N:25]=C=NC2CCCCC2)CCCCC1>CN(C=O)C.CN(C)C1C=CN=CC=1>[NH2:14][CH2:15][C:6]([NH:8][CH2:9][C:10]([NH2:25])=[O:12])=[O:5]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 2723639Glycinamide hydrochloride

Product 1

HCID 437662Glycylglycinamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2 g (11.4 mmole) of N-(tert-butoxycarbonyl)-glycine (Boc-glycine) and 1.26 g (22.8 mmole) of glycinamide hydrochloride in 100 mL of DMF at neutral pH, 3.54 g (17.1 mmole) of dicyclohexylcarbodiimide (DCC) was added and 0.28 g (2.3 mmole) of 4-dimethylaminopyridine (DMAP) was added as a catalyst. The reaction mixture was stirred for 24 hours at room temperature, the insoluble materials were filtered and the filtrate was evaporated to dryness in vacuum.

Workup

  1. filtrationthe insoluble materials were filtered
  2. customthe filtrate was evaporated to dryness in vacuum

Sources & evidence

ORD record
ord-7373b64b9eee4437b59058a5e26d3fc5
Source dataset
uspto-grants-2000_02
Patent number
US06028102

Reaction notes

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