Ammonium formate → (+)-N,N-di(tert-butyloxycarbonyl)-[(4aR*,8aS*)-8a-(4-aminothiophen-2-yl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]amine

HRID 218001

Reaktionsgleichung

Reaktionsgleichung von HRID 218001
C([O-])=O.[NH4+].[C:5]([O:9][C:10]([N:12]([C:20]1[S:29][CH2:28][C@H:27]2[C@:22]([C:30]3[S:31][CH:32]=[C:33]([N:35]=[N+]=[N-])[CH:34]=3)([CH2:23][O:24][CH2:25][CH2:26]2)[N:21]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:11])([CH3:8])([CH3:7])[CH3:6]>CO.[Zn]>[C:5]([O:9][C:10]([N:12]([C:20]1[S:29][CH2:28][C@H:27]2[C@@:22]([C:30]3[S:31][CH:32]=[C:33]([NH2:35])[CH:34]=3)([CH2:23][O:24][CH2:25][CH2:26]2)[N:21]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:11])([CH3:6])([CH3:7])[CH3:8]

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 58406041(+/-)-N,N-di(tert-butyloxycarbonyl)-[(4aR*,8aR*)-8a-(4-azidothiophen-2-yl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]amine

Produkt 1

HCID 67216640(+)-N,N-di(tert-butyloxycarbonyl)-[(4aR*,8aS*)-8a-(4-aminothiophen-2-yl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]amineAusbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Zinc powder (133 mg) and ammonium formate (320 mg) were added to a solution of (±)-N,N-di(tert-butyloxycarbonyl)-[(4aR*,8aR*)-8a-(4-azidothiophen-2-yl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]amine (503 mg) in methanol (76.2 ml). The mixture was stirred at room temperature overnight, and then the solvent was evaporated under reduced pressure at room temperature or lower. Water was added to the residue, and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (325 mg).

Aufarbeitung

  1. customthe solvent was evaporated under reduced pressure at room temperature
  2. additionWater was added to the residue
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c6b3c4107bf74f4fbecd6eb04bf0dcfa
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198269B2

Verknüpfte Notizen

Wird geladen…