Triphenylphosphine → {4-[3,3-Bis-(4-pyridin-3-yl-phenyl)-allylsulfanyl]-2-trifluoromethyl-phenoxy}-acetic acid ethyl ester

HRID 9344

반응식

HRID 9344 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.[N:38]1[CH:43]=[CH:42][CH:41]=[C:40]([C:44]2[CH:49]=[CH:48][C:47]([C:50]([C:54]3[CH:59]=[CH:58][C:57]([C:60]4[CH:61]=[N:62][CH:63]=[CH:64][CH:65]=4)=[CH:56][CH:55]=3)=[CH:51][CH2:52]O)=[CH:46][CH:45]=2)[CH:39]=1.[CH2:66]([O:68][C:69](=[O:83])[CH2:70][O:71][C:72]1[CH:77]=[CH:76][C:75]([SH:78])=[CH:74][C:73]=1[C:79]([F:82])([F:81])[F:80])[CH3:67]>C1COCC1>[CH2:66]([O:68][C:69](=[O:83])[CH2:70][O:71][C:72]1[CH:77]=[CH:76][C:75]([S:78][CH2:52][CH:51]=[C:50]([C:54]2[CH:59]=[CH:58][C:57]([C:60]3[CH:61]=[N:62][CH:63]=[CH:64][CH:65]=3)=[CH:56][CH:55]=2)[C:47]2[CH:46]=[CH:45][C:44]([C:40]3[CH:39]=[N:38][CH:43]=[CH:42][CH:41]=3)=[CH:49][CH:48]=2)=[CH:74][C:73]=1[C:79]([F:80])([F:81])[F:82])[CH3:67]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 219868193,3-Bis-(4-pyridin-3-yl-phenyl)-prop-2-en-1-olHCID 59516001Ethyl [4-sulfanyl-2-(trifluoromethyl)phenoxy]acetate

생성물 1

HCID 69620630{4-[3,3-Bis-(4-pyridin-3-yl-phenyl)-allylsulfanyl]-2-trifluoromethyl-phenoxy}-acetic acid ethyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Triphenylphosphine (138 mg, 0.68 mmol) and ADDP (173 mg, 0.68 mmol) were added to a solution of 3,3-bis-(4-pyridin-3-yl-phenyl)-prop-2-en-1-ol (100 mg, 0.27 mmol) in THF (5 ml) at 0° C. The reaction mixture was stirred for 5 min under nitrogen atmosphere. (4-Mercapto-2-trifluoromethyl-phenoxy)-acetic acid ethyl ester (prepared analogous to procedure in BioOrg. Med. Chem. Lett. 2003, 13, 1517) (92 mg, 0.32 mmol) was slowly added to the reaction mixture and the reaction was stirred for further 2 h at 0° C. The reaction mixture was evaporated and the residue was triturated with ether (2×15 ml). The filtered ether phases were evaporated and purified by column chromatography (eluent: ethyl acetate) to give {4-[3,3-bis-(4-pyridin-3-yl-phenyl)-allylsulfanyl]-2-trifluoromethyl-phenoxy}-acetic acid ethyl ester in 100 mg (60%) yield.

후처리

  1. stirringthe reaction was stirred for further 2 h at 0° C
  2. customThe reaction mixture was evaporated
  3. customthe residue was triturated with ether (2×15 ml)
  4. customThe filtered ether phases were evaporated
  5. custompurified by column chromatography (eluent: ethyl acetate)

출처 및 근거

ORD 기록
ord-c5ebe0b0aed846cc89d4466e7663f9a1
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091245B2

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