Trifluoroacetic acid → Ethyl 5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-2-carboxylate

HRID 1964530노트

반응식

HRID 1964530 반응식
[CH3:1][O:2][CH2:3][C@H:4]([CH3:40])[O:5][C:6]1[CH:7]=[C:8]([C:23]2[N:27](C(OC(C)(C)C)=O)[C:26]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:25][CH:24]=2)[CH:9]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[CH:11]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][CH2:3][C@H:4]([CH3:40])[O:5][C:6]1[CH:7]=[C:8]([C:23]2[NH:27][C:26]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:25][CH:24]=2)[CH:9]=[C:10]([O:12][C:13]2[CH:14]=[CH:15][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:17][CH:18]=2)[CH:11]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 666830251-t-Butyl 2-ethyl 5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-1,2-dicarboxylate

생성물 1

HCID 58065515Ethyl 5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-2-carboxylate수율 81.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

1-t-Butyl 2-ethyl 5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-1,2-dicarboxylate (9.44 g, 16.5 mmol) synthesized in Example (17c) was dissolved in dichloromethane (90 mL), and cooled to 0° C. Trifluoroacetic acid (45 mL) was added dropwise with stirring under nitrogen atmosphere, and stirring was carried out at room temperature for 1 hour. The solvent was distilled off under reduced pressure, followed by dilution with ethyl acetate (300 mL), a saturated aqueous sodium hydrogencarbonate solution (200 mL) was added, and the solution was separated. The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-50%) to afford the desired compound (6.34 g, yield 81%) as a pale yellow solid.

후처리

  1. stirringstirring
  2. distillationThe solvent was distilled off under reduced pressure
  3. additiona saturated aqueous sodium hydrogencarbonate solution (200 mL) was added
  4. customthe solution was separated
  5. washThe organic layer was washed with saturated brine
  6. dry with materialsubsequently dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified
  9. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-50%)

출처 및 근거

ORD 기록
ord-21c5a394009c499387bc76cf6eacde3d
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415359B2

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