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Potassium Carbonate → (S)-tert-butyl 1-cyano-2-(3'-cyanobiphenyl-4-yl)ethylcarbamate

HRID 600293
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 600293
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].[C:12]([C@@H:14]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:15][C:16]1[CH:21]=[CH:20][C:19](I)=[CH:18][CH:17]=1)#[N:13].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.[Cl-].[Na+].O>[C:12]([C@@H:14]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=2)=[CH:18][CH:17]=1)#[N:13]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 57999650(S)-Tert-butyl (1-cyano-2-(4-iodophenyl)ethyl)carbamate

Produkt 1

HCID 57999672(S)-tert-butyl 1-cyano-2-(3'-cyanobiphenyl-4-yl)ethylcarbamateAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel
2×
HCID 312751,4-DioxaneLösungsmittel
HCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A solution of 3-cyanophenylboronic acid (4.74 g), (S)-tert-butyl 1-cyano-2-(4-iodophenyl)ethylcarbamate (10 g) and bis[bis(1,2-diphenylphosphino)-ethane]palladium (0) (0.243 g) in dioxane (100 mL) under nitrogen, was stirred for 10 min. A solution of potassium carbonate (7.43 g) in water (30 mL) was added and the resulting solution was stirred at 75° C. for 3 h. The cooled mixture was poured into water containing brine and extracted with ethyl acetate (3×150 mL). The combined organics were washed with saturated brine (3×50 mL), dried over sodium sulfate and adsorbed onto silica. The crude product was purified by flash silica chromatography, eluting with 20% ethyl acetate in isohexane. Pure fractions were evaporated to dryness to afford (S)-tert-butyl 1-cyano-2-(3′-cyanobiphenyl-4-yl)ethylcarbamate (8.42 g) as a pale yellow solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×150 mL)
  2. washThe combined organics were washed with saturated brine (3×50 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe crude product was purified by flash silica chromatography
  5. washeluting with 20% ethyl acetate in isohexane
  6. customPure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-5e2ea4f11b1a492c822d78036c4699b7
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07902181B2

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