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

HRID 1796622노트

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HRID 1796622 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

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온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-156ffb683a9541208b683c044d09c754
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030112B2

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