Sodium Carbonate → 4,9-Dioxo-2,5,8,11-tetra-azabicyclo[10,4,0]-hexadecane

HRID 1708330Notes

Reaction equation

HRID 1708330 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[NH2:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[NH2:14].[Cl:15][NH:16][CH2:17][CH2:18][N:19]([C:21](=[O:23])[CH3:22])[Cl:20].[OH:24][CH:25]1O[C@@H](CO)[C@H](O)[C@H](O)[C@H:26]1O>C(#N)C>[Cl:15][NH:16][CH2:17][CH2:18][N:19]([C:21](=[O:23])[CH3:22])[Cl:20].[O:23]=[C:21]1[NH:19][CH2:18][CH2:17][NH:16][C:25](=[O:24])[CH2:26][NH:14][CH:9]2[CH:8]([CH2:13][CH2:12][CH2:11][CH2:10]2)[NH:7][CH2:22]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 10219674L-AltroseHCID 18958570N,N'-dichloroacetylethylenediamine

Product 2

HCID 189585644,9-Dioxo-2,5,8,11-tetra-azabicyclo[10,4,0]-hexadecaneHCID 18958570N,N'-dichloroacetylethylenediamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Sodium carbonate (226 g., 2.13 mol.) and trans-1,2-diaminocyclohexane (14.1 ml., 117 mmol.) were added to a solution of N,N'-dichloroacetylethylenediamine (25 g., 117 mmol.) in dry acetonitrile (3.75 l.) under nitrogen. N,N'-dichloroacetylethylenediamine was prepared as reported by Lin W.C., Fiqueira, J. A. D and Alt, H. G. in "New multidentate potential inophors of ether-amide type", Monat. Chem., 1985, 116, 217-221. The reaction mixture was refluxed for 20 hours. The insoluble material formed was filtered off and the volume of the filtrate was reduced to 1 l. by evaporation. Crystals of the compound (A) slowly formed at room temperature. They were collected by filtration and the product was purified by crystallization in acetonitrile. The yield was 7.43 g. of a white solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 20 hours
  2. customThe insoluble material formed
  3. filtrationwas filtered off
  4. customby evaporation

Sources & evidence

ORD record
ord-8e28cbc9ab86402eb73706f7277fa473
Source dataset
uspto-grants-1994_10
Patent number
US05358704

Reaction notes

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