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Hydrochloric Acid → 2-(3-Chloro-4-methanesulfonyl-phenyl)-3-(3-oxo-cyclopentyl)-propionic acid methyl ester

HRID 2214105
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HRID 2214105 반응식
[CH3:1][O:2][C:3](=[O:27])[CH:4]([C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[C:18]([Cl:26])[CH:17]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][C:8]2(OCCC[O:11]2)[CH2:7]1.Cl>O1CCCC1>[CH3:1][O:2][C:3](=[O:27])[CH:4]([C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[C:18]([Cl:26])[CH:17]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7]1
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참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 674820872-(3-Chloro-4-methanesulfonyl-phenyl)-3-(6,10-dioxa-spiro[4.5]dec-2-yl)-propionic acid methyl ester

생성물 1

HCID 674822472-(3-Chloro-4-methanesulfonyl-phenyl)-3-(3-oxo-cyclopentyl)-propionic acid methyl ester수율 99%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
25 °C

실험 절차

A solution of 2-(3-chloro-4-methanesulfonyl-phenyl)-3-(6,10-dioxa-spiro[4.5]dec-2-yl)-propionic acid methyl ester (1.21 g, 2.90 mmol) in tetrahydrofuran (14.5 mL) was treated with a 5% aqueous hydrochloric acid solution (6.4 mL) and stirred at 25° C. for 29 h. The reaction was then concentrated in vacuo to remove tetrahydrofuran. The resulting aqueous residue was diluted with water (200 mL) and extracted with ethyl acetate (2×100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 50% ethyl acetate/hexanes) afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-3-(3-oxo-cyclopentyl)-propionic acid methyl ester (1.03 g, 99%) as a colorless oil: EI-HRMS m/e calcd for C16H19ClO5S (M)+ 358.0642 found 358.0630.

후처리

  1. concentrationThe reaction was then concentrated in vacuo
  2. customto remove tetrahydrofuran
  3. additionThe resulting aqueous residue was diluted with water (200 mL)
  4. extractionextracted with ethyl acetate (2×100 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3910bf3e4ab647c2b50dfc34e0f99e5e
출처 데이터셋
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07105671B2

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