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Ethyl Acetate → 3-{3-Fluoro-4-[1-(4'-trifluoromethyl-biphenyl-4-yl)-heptyloxy]-benzoylamino}-propionic acid ethyl ester

HRID 1669335
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인쇄 미리보기

반응식

HRID 1669335 반응식
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]([OH:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH2:25]([O:27][C:28](=[O:42])[CH2:29][CH2:30][NH:31][C:32](=[O:41])[C:33]1[CH:38]=[CH:37][C:36](O)=[C:35]([F:40])[CH:34]=1)[CH3:26].C(P(CCCC)CCCC)CCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:25]([O:27][C:28](=[O:42])[CH2:29][CH2:30][NH:31][C:32](=[O:41])[C:33]1[CH:38]=[CH:37][C:36]([O:22][CH:15]([C:12]2[CH:13]=[CH:14][C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:23])([F:24])[F:1])=[CH:8][CH:7]=3)=[CH:10][CH:11]=2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[C:35]([F:40])[CH:34]=1)[CH3:26]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 13831TributylphosphineHCID 597294013-(3-Fluoro-4-hydroxy-benzoylamino)-propionic acid ethyl esterHCID 597294131-(4'-Trifluoromethyl-biphenyl-4-yl)-heptan-1-ol

생성물 1

HCID 597293873-{3-Fluoro-4-[1-(4'-trifluoromethyl-biphenyl-4-yl)-heptyloxy]-benzoylamino}-propionic acid ethyl ester수율 90.1%

시약·촉매·용매

1
HCID 1140Toluene용매

실험 절차

Combine 1-(4′-trifluoromethyl-biphenyl-4-yl)-heptan-1-ol (0.257 g, 0.76 mmol) and 3-(3-Fluoro-4-hydroxy-benzoylamino)-propionic acid ethyl ester (0.150 g, 0.59 mmol) in toluene (3.0 mL). Add 1,1′(diazocarbonyl)dipiperidine (0.223 g, 0.88 mmol) followed by tributyl-phosphane (0.22 mL, 0.88 mmol) under inert atmosphere. Stir at room temperature for 18 hours. Dilute reaction with ethyl acetate filter and remove solvent under reduced pressure. Purify on silica gel chromatography (0-70% Ethyl acetate/hexanes gradient) to provide 0.305 g of title compound (90%).

후처리

  1. additionDilute
  2. filtrationfilter
  3. customremove solvent under reduced pressure
  4. customPurify on silica gel chromatography (0-70% Ethyl acetate/hexanes gradient)

출처 및 근거

ORD 기록
ord-bd57321554544770a42a0ec8a0de8175
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07989457B2

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