Pivaloyl chloride → HCID 13532752, compound

HRID 1906259Notes

Reaction equation

HRID 1906259 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].[C:23](Cl)(=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25]>N1C=CC=CC=1>[C:23]([O:20][CH2:19][N:15]1[C:14](=[O:21])[CH2:13][N:12]([CH2:11][CH2:10][N:6]2[CH2:7][C:8](=[O:9])[N:3]([CH2:2][O:1][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:4](=[O:22])[CH2:5]2)[CH2:17][C:16]1=[O:18])(=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 13532751HCID 13532751, compound

Product 1

HCID 13532752HCID 13532752, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a mixture of 1,2-bis(4-hydroxymethyl-3,5-dioxopiperazin-1-yl)ethane (0.94 g, 3.0 m mol) and pyridine (25 ml), pivaloyl chloride (0.78 g, 6.5 m mol) dissolved in pyridine (5 ml) was added gradually at 0° C., and then the mixture was stirred for 18 hours at room temperature. The solvent was removed from the reaction mixture under reduced pressure, and the residue was extracted with ethyl acetate (200 ml). The extract solution was washed with a saturated sodium bicarbonate aqueous solution and successively with water and was dried over magnesium sulfate. The residue obtained by removing the solvent from the extract under reduced pressure was purified by silica gel column chromatography (ethyl acetate, Rf value=0.8) to give the titled compound (0.75 g; yield 52%).

Workup

  1. additionwas added gradually at 0° C.
  2. customThe solvent was removed from the reaction mixture under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate (200 ml)
  4. washThe extract solution was washed with a saturated sodium bicarbonate aqueous solution and successively with water
  5. dry with materialwas dried over magnesium sulfate
  6. customThe residue obtained
  7. customby removing the solvent from the
  8. extractionextract under reduced pressure
  9. customwas purified by silica gel column chromatography (ethyl acetate, Rf value=0.8)

Sources & evidence

ORD record
ord-04211796c9ed4d3ea6b85133609a8344
Source dataset
uspto-grants-1987_03
Patent number
US04650799

Reaction notes

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