Ethyl Acetate → (R)-2-(3-bromo-4-cyanophenylamino)-4-methylpentanamide

HRID 2201035

Reaktionsgleichung

Reaktionsgleichung von HRID 2201035
[Br:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl.[NH2:12][C@@H:13]([C:18]([NH2:20])=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16].CCN(C(C)C)C(C)C.CCOC(C)=O>CS(C)=O.O>[Br:1][C:2]1[CH:9]=[C:8]([NH:12][C@H:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:18]([NH2:20])=[O:19])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 1189392-Bromo-4-fluorobenzonitrileHCID 56776963(R)-2-Amino-4-methylpentanamide hydrochloride

Produkt 1

HCID 67509372(R)-2-(3-bromo-4-cyanophenylamino)-4-methylpentanamideAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 2-bromo-4-fluorobenzonitrile (200 mg, 1.00 mmol), D-leucine amide hydrochloride (200 mg, 1.20 mmol) and DIEA (0.620 mL, 3.56 mmol) in DMSO (3 mL) was stirred at 100 C for 18 h. EtOAc and water were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silicsa gel column, eluted first with 30% EtOAc in hexane, then with 80% EtOAc to give (R)-2-(3-bromo-4-cyanophenylamino)-4-methylpentanamide (187 mg).

Aufarbeitung

  1. customThe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by a silicsa gel column
  5. washeluted first with 30% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-825f13df1c6d4da6b8c8c9a2d1087874
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359375B2

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