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

HRID 1796622ノート

反応式

HRID 1796622 の反応式
[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]

参加物

5

反応物 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 547176541-(2-Ethoxycarbonyl-benzoylamino)-3-hydroxy-1H-pyrrole-2,4-dicarboxylic acid diethyl ester

生成物 1

HCID 693272701-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-methoxy-1H-pyrrole-2,4-dicarboxylic acid diethyl ester収率 75.1%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-156ffb683a9541208b683c044d09c754
出典データセット
uspto-grants-2006_04
特許番号
US07030112B2

反応ノート

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