Acetic Acid → 3-[5-(4-Fluoro-phenyl)-thiophen-2-yl]-propionic acid

HRID 1931391노트

반응식

HRID 1931391 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH:13]=[CH:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CO.C(O)(=O)C>[Pd].O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 887MethanolHCID 534120103-[5-(4-Fluoro-phenyl)-thiophen-2-yl]-acrylic acid

생성물 1

HCID 685366543-[5-(4-Fluoro-phenyl)-thiophen-2-yl]-propionic acid

시약·촉매·용매 2

HCID 23938Palladium촉매2회HCID 8028Tetrahydrofuran용매

실험 절차

40 mg of 5% palladium on carbon were added to a solution of 500 mg (2.0 mmol) of 3-[5-(4-fluoro-phenyl)-thiophen-2-yl]-acrylic acid in 20 ml of tetrahydrofuran, and the reaction mixture was hydrogenated at atmospheric pressure and room temperature for 24 h. 10 ml of methanol and 40 mg of 5% palladium on carbon were added and the reaction mixture was hydrogenated at atmospheric pressure and room temperature for further 24 hours. 10 ml of acetic acid were added and the reaction mixture was hydrogenated at atmospheric pressure and room temperature for another 24 h. The mixture was filtered and evaporated, and the product was purified by preparative RP HPLC eluting with a gradient of 0 to 100% acetonitrile in water (+0.01% TFA). After lyophilization, the product was obtained as a solid. Yield: 400 mg.

후처리

  1. waitthe reaction mixture was hydrogenated at atmospheric pressure and room temperature for further 24 hours
  2. waitthe reaction mixture was hydrogenated at atmospheric pressure and room temperature for another 24 h
  3. filtrationThe mixture was filtered
  4. customevaporated
  5. customthe product was purified by preparative RP HPLC
  6. washeluting with a gradient of 0 to 100% acetonitrile in water (+0.01% TFA)
  7. customAfter lyophilization, the product was obtained as a solid

출처 및 근거

ORD 기록
ord-aa7e0e955ce84d579f2f86795143aa50
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188291B2

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