Methanol → 4-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(2-amino-1-aminomethyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amide

HRID 408929Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 408929
[N:1]([CH2:4][CH:5]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([C:19]2[N:20]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:21]=[C:22]([C:24]#[N:25])[N:23]=2)=[O:18])=[C:12]([C:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH:35]=2)[CH:11]=1)[CH2:6][N:7]=[N+]=[N-])=[N+]=[N-].O.CO.[NH4+].[Cl-]>C1COCC1.[Zn]>[NH2:7][CH2:6][CH:5]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([C:19]2[N:20]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:31])[CH3:32])[CH:21]=[C:22]([C:24]#[N:25])[N:23]=2)=[O:18])=[C:12]([C:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH:35]=2)[CH:11]=1)[CH2:4][NH2:1]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 866158984-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(2-azido-1-azidomethyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amide

Produkt 1

HCID 597712334-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(2-amino-1-aminomethyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amideAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(2-azido-1-azidomethyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amide (as prepared above, 546 mg, 1.00 mmol) was dissolved in THF (1 mL), water (2 mL) and MeOH (10 mL). To this solution NH4Cl (534 mg, 25.0 mmol) and Zn powder (653 mg, 10.0 mmol) were added with cooling. The resulting mixture was stirred at RT for 30 min and filtered through a thin pad of Celite. The filter cake was washed with MeOH (2×10 mL). The filtrate was concentrated, dissolved in 5% i-PrOH/DCM and washed with satd aq NaHCO3 (20 mL). The organic layer was dried (Na2SO4) and concentrated to obtain the title compound (207 mg, 42%): Mass spectrum (ESI, m/z): Calcd. for C26H38N6O2Si, 495.3 (M+H). found 495.2.

Aufarbeitung

  1. temperaturewith cooling
  2. filtrationfiltered through a thin pad of Celite
  3. washThe filter cake was washed with MeOH (2×10 mL)
  4. concentrationThe filtrate was concentrated
  5. dissolutiondissolved in 5% i-PrOH/DCM
  6. washwashed with satd aq NaHCO3 (20 mL)
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d878d9f296d5449d95c473dbd48a1a90
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759347B2

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