Triphenylphosphine → tert-butyl (6S,7S)-7-(4-chloro-3-fluorophenyl)-6-[(3-cyanopyridin-2-yl)oxy]-1,4-oxazepane-4-carboxylate

HRID 1022831

Reaktionsgleichung

Reaktionsgleichung von HRID 1022831
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C@@H:22]2[O:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24][C@H:23]2[OH:36])=[CH:18][C:17]=1[F:37].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O=[C:58]1[C:63]([C:64]#[N:65])=[CH:62][CH:61]=[CH:60][NH:59]1>O1CCCC1.O>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C@@H:22]2[O:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])[CH2:24][C@@H:23]2[O:36][C:58]2[C:63]([C:64]#[N:65])=[CH:62][CH:61]=[CH:60][N:59]=2)=[CH:18][C:17]=1[F:37]

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 5775433-Cyano-2-pyridoneHCID 66976341tert-butyl (6R,7S)-7-(4-chloro-3-fluorophenyl)-6-hydroxy-1,4-oxazepane-4-carboxylate

Produkt 1

HCID 66976656tert-butyl (6S,7S)-7-(4-chloro-3-fluorophenyl)-6-[(3-cyanopyridin-2-yl)oxy]-1,4-oxazepane-4-carboxylateAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Diisopropyl azodicarboxylate (1.9 M in toluene, 0.69 mL) was added dropwise to a solution of tert-butyl (6R,7S)-7-(4-chloro-3-fluorophenyl)-6-hydroxy-1,4-oxazepane-4-carboxylate (300 mg), triphenylphosphine (340 mg) and 2-oxo-1,2-dihydropyridine-3-carbonitrile (160 mg) in tetrahydrofuran (10 mL), and the mixture was stirred at room temperature for 4 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (250 mg).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ff26bb7785f54bb2bc00919d2c121f20
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722662B2

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