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

HRID 84837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 84837
[F:1][C:2]1[C:9]([F:10])=[C:8](F)[CH:7]=[CH:6][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[CH:6]=[CH:7][C:8]([NH:13][C@H:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:19]([NH2:21])=[O:20])=[C:9]([F:10])[C:2]=1[F:1])#[N:5]

Komponenten

7

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 5189362,3,4-TrifluorobenzonitrileHCID 56776963(R)-2-Amino-4-methylpentanamide hydrochloride

Produkt 1

HCID 67508536(R)-2-(4-cyano-2,3-difluorophenylamino)-4-methylpentanamideAusbeute 25,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 2,3,4-trifluorobenzonitrile (265 mg, 1.68 mmol) in a flask, a solution of D-leucine amide hydrochloride (282 mg, 1.68 mmol) and DIEA (0.880 mL, 5.06 mmol) in DMSO (5 mL) was added. After being stirred at room temperature for 68 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 0-70% EtOAc in hexane to give (R)-2-(4-cyano-2,3-difluorophenylamino)-4-methylpentanamide (113 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 0-70% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-0b83fb02c60e4ad180272dabc7207d89
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846928B2

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