Hydrogen Peroxide → Ethyl 3-(((benzyloxy)carbonyl)amino)-2,5-dioxopyrrolidine-3-carboxylate

HRID 256600Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:25])[C:5]([NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])([C:12]#[N:13])[CH2:6][C:7](OCC)=[O:8])[CH3:2].[OH:26]O.[OH-].[Na+]>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:18]([O:17][C:15]([NH:14][C:5]1([C:4]([O:3][CH2:1][CH3:2])=[O:25])[CH2:6][C:7](=[O:8])[NH:13][C:12]1=[O:26])=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-benzyloxycarbonylamino-2-cyanosuccinic acid diethyl ester (15.4 g) in dichloromethane (50 ml) was cooled to ice-bath temperature, and then 30% hydrogen peroxide (21 ml), tetrabutylammonium hydrogen sulfate (3.0 g) and 20% aqueous sodium hydroxide solution (16.6 ml) were added in turn. The resulting mixture was stirred under ice cooling for 30 minutes and then at 25° C. for 1 hour. The organic layer was separated, washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was heated at 80° C. for 1.5 hours to give the title compound (11.5 g, 81.2%), which was recrystallized from ethyl acetate/n-hexane to give the pure product, mp 105°-106° C.

Workup

waitat 25° C. for 1 hour
customThe organic layer was separated
washwashed with water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-c658de155a7e49878b67932f9f1167a0
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05258382

Reaction notes

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