Tetrahydrofuran → 6-[1,3-dihydroxy-1-(1-trityl-1H-imidazol-4-yl)propyl]-N-methyl-2-naphthamide

HRID 2044774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2044774
C1COCC1.[BH4-].[Na+].[OH:8][C@@:9]([C:41]1[CH:50]=[CH:49][C:48]2[C:43](=[CH:44][CH:45]=[C:46]([C:51]([NH:53][CH3:54])=[O:52])[CH:47]=2)[CH:42]=1)([C:17]1[N:18]=[CH:19][N:20]([C:22]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=1)[CH2:10][C:11](OC(C)C)=[O:12].[Cl-].[NH4+]>[Cl-].[Zn+2].[Cl-].C(OCC)(=O)C.O>[OH:8][C:9]([C:41]1[CH:42]=[C:43]2[C:48](=[CH:49][CH:50]=1)[CH:47]=[C:46]([C:51]([NH:53][CH3:54])=[O:52])[CH:45]=[CH:44]2)([C:17]1[N:18]=[CH:19][N:20]([C:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=1)[CH2:10][CH2:11][OH:12]

Komponenten

8

Edukt 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 57465811isopropyl(3S)-3-hydroxy-3-{6-[(methylamino)carbonyl]-2-naphthyl}-3-(1-trityl-1H-imidazol-4-yl)propanoate

Produkt 1

HCID 101530586-[1,3-dihydroxy-1-(1-trityl-1H-imidazol-4-yl)propyl]-N-methyl-2-naphthamideAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855ZincchlorideKatalysatorHCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

3 mL of THF and 0.17 g (1.25 mmol, 8 eq) of zinc chloride were added to 0.095 g (2.51 mmol, 8 eq) of sodium borohydride. The mixture was stirred at 25° C. for 10 minutes. 0.2 g (0.31 mmol) of isopropyl (3S)-3-hydroxy-3-{6-[(methylamino)carbonyl]-2-naphthyl}-3-(1-trityl-1H-imidazol-4-yl)propanoate was added. The mixture was stirred at 40° C. for 31 hours. After cooled to 25° C., 3 droplets of water was added dropwise, 11 mL of water, 1 mL of an aqueous saturated ammonium chloride solution and 12 mL of ethyl acetate were added, and the layers were separated. The organic layer was washed successively with a mixed solution of 1 mL of an aqueous saturated ammonium chloride solution and 8 mL of water, and 8 mL of water 2 times. After concentrated under reduced pressure, the concentration residue was loosened with 4 mL of water, and crystals were filtered. Vacuum drying (40° C.) to a constant weight afforded 0.15 g of 6-[1,3-dihydroxyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-N-methyl-2-naphthamide (yield 76%).

Aufarbeitung

  1. stirringThe mixture was stirred at 40° C. for 31 hours
  2. temperatureAfter cooled to 25° C.
  3. customthe layers were separated
  4. washThe organic layer was washed successively with a mixed solution of 1 mL of an aqueous saturated ammonium chloride solution and 8 mL of water, and 8 mL of water 2 times
  5. concentrationAfter concentrated under reduced pressure
  6. filtrationwere filtered
  7. customVacuum drying (40° C.) to a constant weight

Quellen und Nachweise

ORD-Eintrag
ord-6a6425a7476c42649b25b5a17af37619
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586762B2

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