Triphenylphosphine → HCID 178489999, 화합물

HRID 1627295노트

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HRID 1627295 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([S:23][CH2:24][C:25]3[C:34]([F:35])=[CH:33][C:28]([O:29][CH2:30][CH2:31]O)=[CH:27][C:26]=3[F:36])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:37][CH3:38].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:58]([O:62][C:63]([NH:65][C:66]([NH:68][C:69]([O:71][C:72]([CH3:75])([CH3:74])[CH3:73])=[O:70])=[NH:67])=[O:64])([CH3:61])([CH3:60])[CH3:59].CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.CCOC(C)=O>[C:72]([O:71][C:69](=[O:70])[N:68]=[C:66]([NH:65][C:63]([O:62][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:64])[NH:67][CH2:31][CH2:30][O:29][C:28]1[CH:33]=[C:34]([F:35])[C:25]([CH2:24][S:23][C:14]2[N:15]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[C:11]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:37][CH3:38])[CH:4]=3)([CH3:10])[CH3:9])=[CH:12][N:13]=2)=[C:26]([F:36])[CH:27]=1)([CH3:75])([CH3:74])[CH3:73]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 667407372-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)ethanolHCID 135638421tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanimidoyl)carbamate

생성물 1

HCID 178489999HCID 178489999, 화합물수율 128.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)ethanol (153 mg, 0.27 mmol) in THF (0.39 mL) were added PPh3 (107 mg, 0.41 mmol), 1,3-bis(tert-butoxycarbonyl)guanidine (144 mg, 0.55 mmol) and DIAD (85 μL, 0.41 mmol). After stirring overnight, the reaction mixture was diluted with EtOAc, washed with H2O and brine, dried over Na2SO4 and concentrated. The crude material was purified by flash chromatography (80% EtOAc/hexanes) to afford tert-butyl(tert-butoxycarbonylamino)(2-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)ethylamino)methylenecarbamate (279 mg), which was taken to the final step without further purification. MS (EI) m/z 804.5 (MH+).

후처리

  1. washwashed with H2O and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude material was purified by flash chromatography (80% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-a6da18767eb041c598399ef47da28999
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785488B2

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