Dimethyl Sulfate → 1-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-methoxy-1H-pyrrole-2,4-dicarboxylic acid diethyl ester

HRID 1796622Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[N:7]([NH:17][C:18](=[O:30])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25](OCC)=[O:26])[CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]=1[OH:11])=[O:5])[CH3:2].[C:31]([O-])([O-])=O.[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([N:17]2[C:18](=[O:30])[C:19]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:25]2=[O:26])[CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]=1[O:11][CH3:31])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 393C (0.84 g, 2 mmol) and K2CO3 (1.0 g, 7.25 mmol) in acetone (5 ml) was heated at 50° C. for 30 min, then cooled to rt. Dimethyl sulfate (0.29 ml, 3.0 mmol) was added, the resulting mixture was heated at 40° C. until starting material consumed, quenched with brine and extracted with EtOAc. The organic layer was dried and concentrated, the residue was purified by silica gel flash column chromatography to afford 393D (0.58 g, 74% for 3 steps from 393B) (0%-5% EtOAc—CH2Cl2).

Workup

temperaturecooled to rt
temperaturethe resulting mixture was heated at 40° C.
customconsumed
customquenched with brine
extractionextracted with EtOAc
customThe organic layer was dried
concentrationconcentrated
customthe residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record: ord-156ffb683a9541208b683c044d09c754
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030112B2

Reaction notes

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