Pyridine → HCID 20212771, compound

HRID 1906260Notes

Reaction equation

HRID 1906260 reaction equation
[OH:1][CH2:2][N:3]1[C:8](=[O:9])[CH2:7][N:6]([CH2:10][CH2:11][N:12]2[CH2:17][C:16](=[O:18])[N:15]([CH2:19][OH:20])[C:14](=[O:21])[CH2:13]2)[CH2:5][C:4]1=[O:22].N1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH:29]1([C:35](Cl)=[O:36])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.C([O:41][CH2:42][CH3:43])(=O)C>>[CH:29]1([C:35]([O:20][CH2:19][N:15]2[C:14](=[O:21])[CH2:13][N:12]([CH2:11][CH2:10][N:6]3[CH2:7][C:8](=[O:9])[N:3]([CH2:2][O:1][C:42]([CH:43]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)=[O:41])[C:4](=[O:22])[CH2:5]3)[CH2:17][C:16]2=[O:18])=[O:36])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

5

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 75938Cyclohexanecarbonyl chlorideHCID 13532751HCID 13532751, compound

Product 1

HCID 20212771HCID 20212771, compoundYield 30%

Procedure

To a mixture of 1,2-bis(4-hydroxymethyl-3,5-dioxopiperazin-1-yl)ethane (0.32 g, 1.0 m mol) and pyridine (9 ml), cyclohexanecarbonyl chloride (0.3 ml, 2.2 m mol) was added gradually, and then the mixture was stirred for 12 hours at room temperature. The reaction mixture was diluted with ethyl acetate (100 ml) and was washed with 10% sulfuric acid solution and successively with water and was dried. The crude product obtained by removing the solvent under reduced pressure from the above mixture was purified by silica gel column chromatography (ethyl acetate: chloroform=2:1, Rf value=0.6) to give the oily titled compound (0.16 g, yield 30%).

Workup

  1. additionwas added gradually
  2. washwas washed with 10% sulfuric acid solution and successively with water
  3. customwas dried
  4. customThe crude product obtained
  5. customby removing the solvent under reduced pressure from the above mixture
  6. customwas purified by silica gel column chromatography (ethyl acetate: chloroform=2:1, Rf value=0.6)

Sources & evidence

ORD record
ord-23c0bf25cf0e44379bf58364fa69520e
Source dataset
uspto-grants-1987_03
Patent number
US04650799

Reaction notes

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