Potassium Carbonate → (S)-tert-Butyl 1-amino-3-(4'-cyanobiphenyl-4-yl)-1-oxopropan-2-ylcarbamate

HRID 216909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 216909
[NH2:1][C:2](=[O:20])[C@@H:3]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1.[C:21]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)#[N:22].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[NH2:1][C:2](=[O:20])[C@@H:3]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:26]2[CH:27]=[CH:28][C:23]([C:21]#[N:22])=[CH:24][CH:25]=2)=[CH:7][CH:6]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 57999635(S)-tert-Butyl (1-amino-3-(4-iodophenyl)-1-oxopropan-2-yl)carbamate

Produkt 1

HCID 59568594(S)-tert-Butyl 1-amino-3-(4'-cyanobiphenyl-4-yl)-1-oxopropan-2-ylcarbamateAusbeute 105,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

(S)-tert-Butyl 1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamate (Example 3, step (i), 3.17 g) and 4-cyanophenylboronic acid (1.19 g) in dioxane (5 mL) were treated with 1,1 bis(di-tert-butylphosphino)ferrocene palladium dichloride (0.08 g) and the mixture was stirred at room temperature for 15 min under nitrogen. An aqueous solution of potassium carbonate (2M, 8.12 mL) was added and the mixture was stirred for 18 h at 75° C. The reaction mixture was extracted with ethyl acetate, dried and evaporated to afford the sub-titled compound (3.13 g).

Aufarbeitung

  1. stirringthe mixture was stirred for 18 h at 75° C
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. customdried
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f2035795ecc84f52939f3fe74f2056fc
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193239B2

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