Water → (R)-3-(benzyloxy)-2-(3-bromo-4-cyanophenylamino)propanamide

HRID 2201050

Reaktionsgleichung

Reaktionsgleichung von HRID 2201050
[Br:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH2:11]([O:18][CH2:19][C@H:20]([C:22]([NH2:24])=[O:23])[NH2:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(C(C)C)C(C)C.O>CS(C)=O.CCOC(C)=O>[CH2:11]([O:18][CH2:19][C@@H:20]([NH:21][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([Br:1])[CH:9]=1)[C:22]([NH2:24])=[O:23])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 1189392-Bromo-4-fluorobenzonitrileHCID 58987402O-benzyl-D-serinamide

Produkt 1

HCID 67509048(R)-3-(benzyloxy)-2-(3-bromo-4-cyanophenylamino)propanamideAusbeute 17,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 2-bromo-4-fluorobenzonitrile (200 mg, 1.00 mmol), O-benzyl-D-serinamide (290 mg, 1.49 mmol) and DIEA (0.466 mL, 2.68 mmol) in DMSO (3 mL) was stirred at 100 C for 18 h. Water and EtOAc were added. The organic phase was separated, washed with 1N HCl, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with 0-60% EtOAc in hexane to give (R)-3-(benzyloxy)-2-(3-bromo-4-cyanophenylamino)propanamide (66 mg).

Aufarbeitung

  1. customThe organic phase was separated
  2. washwashed with 1N HCl
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a silica gel column
  6. washeluted with 0-60% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-7b1a324529b0441bba81e652b653dea6
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359375B2

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