Dicyclohexylcarbodiimide → HCID 15053735, compound

HRID 477205Notes

Reaction equation

HRID 477205 reaction equation
Cl.[NH2:2][CH:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH:14]([NH:16][CH2:17][C:18](O)=[O:19])=[O:15].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O.C(N(CC)CC)C>[CH:14]([NH:16][CH2:17][C:18]([NH:2][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:19])=[O:15]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 75606FormylglycineHCID 757711-HydroxybenzotriazoleHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)

Product 1

HCID 15053735HCID 15053735, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Diethyl 2-aminomalonate hydrochloride (4.2 g), formylglycine (2.3 g) and 1-hydroxybenzotriazole (2.7 g) are dissolved in dimethylformamide (50 ml). To the solution are added N,N'-dicyclohexylcarbodiimide (4.33 g) and triethylamine (2.12 g) at 0° to 5° C. The mixture is stirred at the same temperature for 2 hours and at room temperature for 15 hours. The reaction mixture is concentrated under reduced pressure. To the residue is added ethyl acetate, and the mixture is filtered to remove insoluble materials. The filtrate is washed, dried and evaporated to remove the solvent. The residue is purified by silica gel column chromatography [solvent; chloroform-ethyl acetate (1:5)]to give diethyl 2-[(N-formylglycyl)amino]malonate (4.1 g), m.p. 95°-96° C.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. additionTo the residue is added ethyl acetate
  3. filtrationthe mixture is filtered
  4. customto remove insoluble materials
  5. washThe filtrate is washed
  6. customdried
  7. customevaporated
  8. customto remove the solvent
  9. customThe residue is purified by silica gel column chromatography [solvent

Sources & evidence

ORD record
ord-ea779bf209574b1b9b9e2b0f4389dc5b
Source dataset
uspto-grants-1989_12
Patent number
US04886894

Reaction notes

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