Diphenyl N-Cyanocarbonimidate → HCID 178512234, Verbindung

HRID 1500352Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1500352
[C:1]([N:3]=[C:4]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH:5][C:6]1[CH:7]=[CH:8][C:9]2[CH2:15][CH2:14][CH:13]([NH:16]C(OC(C)(C)C)=O)[CH2:12][CH2:11][C:10]=2[CH:24]=1)#[N:2].C1C=CC(OC(OC2C=CC=CC=2)=NC#N)=CC=1>C(O)(C)C.[H][H].[Pd]>[C:1]([N:3]=[C:4]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH:5][C:6]1[CH:7]=[CH:8][C:9]2[CH2:15][CH2:14][C@H:13]([NH2:16])[CH2:12][CH2:11][C:10]=2[CH:24]=1)#[N:2]

Komponenten

5

Edukt 2

HCID 688090Diphenyl N-CyanocarbonimidateHCID 178452634HCID 178452634, Verbindung

Produkt 1

HCID 178512234HCID 178512234, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178506449HCID 178506449, VerbindungKatalysatorHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

The single enantiomer was then BOC-protected, the nitro group reduced by treatment with H2/Pd and the primary aniline treated with diphenyl cyanocarbonimidate (slight excess) in 20 mL of isopropanol with stirring at ambient temperature overnight. The solid was filtered, washed with isopropanol and ether and dried to give phenyl (7S)—N′-cyano-N-(7-amino-6,7,8,9-tetrahydro-5H-benzo[7]annulene-2-yl)carbamimidate, as a white solid in high yield (from the single enantiomer via transamination).

Aufarbeitung

  1. filtrationThe solid was filtered
  2. washwashed with isopropanol and ether
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-bac8a748b96c477a93855a46d68e18da
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206161B2

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