Triethylamine → 2-{[(Benzyloxy)(hydroxy)methylidene]amino}-N-(1,3-diethoxy-1,3-dioxopropan-2-yl)ethanimidic acid

HRID 477206Notes

Reaction equation

HRID 477206 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].[CH2:14]([O:21][C:22]([NH:24][CH2:25][C:26](O)=[O:27])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH2:14]([O:21][C:22]([NH:24][CH2:25][C:26]([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:27])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 14349BenzyloxycarbonylglycineHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)

Product 1

HCID 2246942-{[(Benzyloxy)(hydroxy)methylidene]amino}-N-(1,3-diethoxy-1,3-dioxopropan-2-yl)ethanimidic acidYield 87.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of diethyl 2-aminomalonate hydrochloride (10.6 g) in tetrahydrofuran are added N-(benzyloxycarbonyl)glycine (10.5 g) and triethylamine (5.1 g). The mixture is cooled to 0° to 5° C., and thereto is added N,N'-dicyclohexylcarbodiimide (10.8 g). The mixture is stirred at the same temperature for 2 hours and then allowed to stand at room temperature overnight. Insoluble substance is filtered off from the reaction mixture. The filtrate is distilled to remove the solvent, and to the residue is added ethyl acetate, and the insoluble substance is filtered off. The filtrate is concentrated under reduced pressure, and the residue is recrystallized from ethyl acetate-isopropyl ether to give diethyl 2-[[N-(benzyloxycarbonyl)glycyl]amino]malonate (16.0 g), m.p. 94.5°-95.5° C.

Workup

  1. temperatureThe mixture is cooled to 0° to 5° C.
  2. waitto stand at room temperature overnight
  3. filtrationInsoluble substance is filtered off from the reaction mixture
  4. distillationThe filtrate is distilled
  5. customto remove the solvent
  6. additionto the residue is added ethyl acetate
  7. filtrationthe insoluble substance is filtered off
  8. concentrationThe filtrate is concentrated under reduced pressure
  9. customthe residue is recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-3b860e0bf4a74aaa8aa23a9a1f89b0ab
Source dataset
uspto-grants-1989_12
Patent number
US04886894

Reaction notes

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