1,2-Dichloroethane → (R)-2-(3-bromo-4-cyanophenylamino)-2-phenylacetamide

HRID 2201059

Reaktionsgleichung

Reaktionsgleichung von HRID 2201059
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12](O)=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].C1C=C2[N:27]=NN(O)C2=CC=1.O.C(Cl)CCl.[NH4+].[OH-]>CN(C=O)C.CCOC(C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]([NH2:27])=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Komponenten

8

Edukt 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67509737HCID 67509737, Verbindung

Produkt 1

HCID 67508351(R)-2-(3-bromo-4-cyanophenylamino)-2-phenylacetamideAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (R)-2-(3-bromo-4-cyanophenylamino)-2-phenylacetic acid (90 mg, 0.27 mmol) and HOBt hydrate (62 mg, 0.40 mmol) in DMF (2 mL), EDC (74 mg, 0.38 mmol) was added. The mixture was stirred for 60 min. Then conc. NH4OH (0.100 mL, ˜1.40 mmol) was added. It was stirred for 18 h. Water and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give (R)-2-(3-bromo-4-cyanophenylamino)-2-phenylacetamide (78 mg).

Aufarbeitung

  1. stirringIt was stirred for 18 h
  2. customThe organic phase was separated
  3. washwashed with 5% NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c375bb37bce748f28dca743fb23e9aaa
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359375B2

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