Hexachloroethane → 4-[1-Phenyl-1-(5-(N-(9-fluorenylmethoxycarbonyl)azetidin-3-yl)-1,3,4-oxadiazol-2-yl)methylene]piperidine-1-carboxylic acid tert-butyl ester

HRID 1394442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1394442
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:15]([NH:17][NH:18][C:19]([CH:21]2[CH2:24][N:23]([C:25]([O:27][CH2:28][CH:29]3[C:41]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[C:35]4[C:30]3=[CH:31][CH:32]=[CH:33][CH:34]=4)=[O:26])[CH2:22]2)=[O:20])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.ClC(Cl)(Cl)C(Cl)(Cl)Cl>CC#N>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11](=[C:14]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:15]2[O:20][C:19]([CH:21]3[CH2:22][N:23]([C:25]([O:27][CH2:28][CH:29]4[C:41]5[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=5[C:35]5[C:30]4=[CH:31][CH:32]=[CH:33][CH:34]=5)=[O:26])[CH2:24]3)=[N:18][N:17]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 6214HexachloroethaneHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 670464624-[1-Phenyl-1-(2-(N-(9-fluorenylmethoxycarbonyl)-3-azetidinecarbonyl)-hydrazinocarbonyl)-methylene]-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 670463744-[1-Phenyl-1-(5-(N-(9-fluorenylmethoxycarbonyl)azetidin-3-yl)-1,3,4-oxadiazol-2-yl)methylene]piperidine-1-carboxylic acid tert-butyl esterAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 4-[1-phenyl-1-(2-(N-(9-fluorenylmethoxycarbonyl)-3-azetidinecarbonyl)-hydrazinocarbonyl)-methylene]-piperidine-1-carboxylic acid tert-butyl ester(0.411 g, 0.645 mmol), iPr2NEt (0.775 mL, 4.448 mmol) and PPh3 (0.693 g, 2.643 mmol) in CH3CN (8 mL) was added hexachloroethane (0.351 mg, 1.483 mmol). The mixture was allowed to stir for 1 h and then it was worked up as in Method A above and the crude product purified by flash chromatography (SiO2/EtOAc-hexane, 1:1) to give the title compound (0.299 g, 75%) as a colorless solid:

Aufarbeitung

  1. customthe crude product purified by flash chromatography (SiO2/EtOAc-hexane, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-0766c824caa5415190bc3f7f3750c65b
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348337B2

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