Pyridine → Carbonic acid, 1,2-ethanediylbis((2,6-dioxo-4,1-piperazinediyl)methylene)dimethyl ester

HRID 1906264Notes

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].N1C=CC=CC=1.Cl[C:30]([O:32][CH3:33])=[O:31]>O>[CH3:33][O:32][C:30]([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:30]([O:32][CH3:33])=[O:31])[C:4](=[O:22])[CH2:5]2)[CH2:17][C:16]1=[O:18])=[O:31]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 1,2-bis(4-hydroxymethyl-3,5-dioxopiperazin-1-yl)ethane (2.20 g, 7.0 m mol) and pyridine (20 ml), methyl chloroformate (1.41 g, 14.9 m mol) was added gradually at 0° C., and the mixture was stirred for 1.5 hours at 0° C., then successively for 3 hours at room temperature. The reaction mixture was added to water and was extracted with chloroform. The extract solution was washed with 10% sulfuric acid solution and successively with water, and was dried over magnesium sulfate. The crystals obtained by concentrating the extract solution under reduced pressure were washed with ethyl acetate and dried under reduced pressure to give the titled compound (1.76 g; yield 58.6%).

Workup

additionwas added gradually at 0° C.
waitsuccessively for 3 hours at room temperature
extractionwas extracted with chloroform
washThe extract solution was washed with 10% sulfuric acid solution and successively with water
dry with materialwas dried over magnesium sulfate
customThe crystals obtained
concentrationby concentrating the extract solution under reduced pressure
washwere washed with ethyl acetate
customdried under reduced pressure

Sources & evidence

ORD record: ord-42525b7a83cc41bcba33e31d36219e00
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04650799

Reaction notes

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