(R)-3,3-Dimethyl-2-aminobutane → (+)-(R)-4-[3,4-dioxo-2-(1,2,2-trimethyl-propylamino)-cyclobut-1-enylamino]-benzonitrile

HRID 260796

Reaktionsgleichung

Reaktionsgleichung von HRID 260796
[O:1]=[C:2]1[C:5](=O)[C:4]([NH:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[C:3]1[O:16]CC.[CH3:19][C@@H:20]([NH2:25])[C:21]([CH3:24])([CH3:23])[CH3:22]>C(O)C>[O:1]=[C:2]1[C:3](=[O:16])[C:4]([NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=2)=[C:5]1[NH:25][C@H:20]([CH3:19])[C:21]([CH3:24])([CH3:23])[CH3:22]

Komponenten

4

Edukt 2

HCID 5324845(R)-3,3-Dimethyl-2-aminobutaneHCID 108240584-[(2-Ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino]benzonitrile

Produkt 1

HCID 10613948(+)-(R)-4-[3,4-dioxo-2-(1,2,2-trimethyl-propylamino)-cyclobut-1-enylamino]-benzonitrileAusbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4-(3,4-Dioxo-2-ethoxy-cyclobut-1-enylamino)-benzonitrile (1 g, 4.1 mmol) and a solution of (R)-1,2,2-trimethylpropylamine (8.2 mmol) in ethanol (50 mL) were stirred at room temperature for 24 hours. The resulting yellow slurry was filtered and rinsed with ethyl acetate to yield 0.92 g (75%) of (+)-(R)-4-[3,4-dioxo-2-(1,2,2-trimethyl-propylamino)-cyclobut-1-enylamino]-benzonitrile as a yellow solid: spectral data was identical to the product of Example 1, paragraph 2, except with [α]D25 =+12° (DMSO, c 0.009).

Aufarbeitung

  1. filtrationThe resulting yellow slurry was filtered
  2. washrinsed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-bdb368b71c6144d4a51e82edda09a65e
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05530025

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