Diisopropylethylamine → HCID 86688376, Verbindung

HRID 1431881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1431881
[Br:1][C:2]1[NH:6][C:5]([C@@H:7]2[CH2:11][C@H:10]([CH3:12])[CH2:9][N:8]2[C:13]([O:15]C(C)(C)C)=O)=[N:4][CH:3]=1.[CH3:20][O:21][C:22]([NH:24][C@@H:25]([C@@H:29]([CH3:32])[CH2:30][CH3:31])C(O)=O)=[O:23].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>Cl.CCO.CN(C=O)C>[Br:1][C:2]1[NH:6][C:5]([C@@H:7]2[CH2:11][C@H:10]([CH3:12])[CH2:9][N:8]2[C:13](=[O:15])[C@@H:25]([NH:24][C:22](=[O:23])[O:21][CH3:20])[C@@H:29]([CH3:32])[CH2:30][CH3:31])=[N:4][CH:3]=1

Komponenten

9

Edukt 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 28378062L-Isoleucine, N-(methoxycarbonyl)-HCID 69675472HCID 69675472, Verbindung

Produkt 1

HCID 86688376HCID 86688376, VerbindungAusbeute 1.786,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(2S,4S)-tert-butyl 2-(5-bromo-1H-imidazol-2-yl)-4-methylpyrrolidine-1-carboxylate (100 mg, 0.13 mmol) in 1.25 N HCl in EtOH (15 mL) was heated to 50° C. for 3 h and then concentrated under reduced pressure. The crude residue was treated with (2S,3S)-2-(methoxycarbonylamino)-3-methylpentanoic acid (625 mg, 3.30 mmol), HATU (1.05 g, 2.77 mmol) and DMF (10 mL), then DIPEA (1.33 mL, 7.62 mmol) was added dropwise. After 2 h, the mixture was poured into saturated aqueous NaHCO3 and then extracted with EtOAc. The organic phase was washed successively with 5% aqueous LiCl and Brine. The organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (30 to 90% of 10% MeOH/EtoAc to Hexanes) afforded methyl (2S,3S)-1-((2S,4S)-2-(5-bromo-1H-imidazol-2-yl)-4-methylpyrrolidin-1-yl)-3-methyl-1-oxopentan-2-ylcarbamate (932 mg, 81%).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed successively with 5% aqueous LiCl and Brine
  4. dry with materialThe organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by silica column chromatography (30 to 90% of 10% MeOH/EtoAc to Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-79b91fbc37124e90aec464c3207c16ee
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940718B2

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