Water → (R)-2-(4-cyano-3,5-difluorophenylamino)-4-methylpentanamide

HRID 84830

Reaktionsgleichung

Reaktionsgleichung von HRID 84830
[F:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[C:6]([F:11])[C:3]=1[C:4]#[N:5].Cl.[NH2:13][C@@H:14]([C:19]([NH2:21])=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17].CCN(C(C)C)C(C)C.O>CS(C)=O.CCOC(C)=O>[C:4]([C:3]1[C:2]([F:1])=[CH:9][C:8]([NH:13][C@H:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:19]([NH2:21])=[O:20])=[CH:7][C:6]=1[F:11])#[N:5]

Komponenten

7

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 7371772,4,6-TrifluorobenzonitrileHCID 56776963(R)-2-Amino-4-methylpentanamide hydrochloride

Produkt 1

HCID 67509019(R)-2-(4-cyano-3,5-difluorophenylamino)-4-methylpentanamideAusbeute 26,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2,4,6-trifluorobenzonitrile (208 mg, 1.32 mmol) in DMSO (2 mL), a solution of D-leucine amide hydrochloride (220 mg, 1.32 mmol) and DIEA (0.688 mL, 3.96 mmol) in DMSO (5 mL) was added. After being stirred at room temperature for 18 h, water and EtOAc were added. The organic phase was separated, washed with water, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with 20-80% EtOAc in hexane to give (R)-2-(4-cyano-3,5-difluorophenylamino)-4-methylpentanamide (92 mg).

Aufarbeitung

  1. customThe organic phase was separated
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a silica gel column
  6. washeluted with 20-80% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-71e08a4bb760452385e7a27395a1cdd3
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846928B2

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