Water → HCID 178443794, Verbindung

HRID 275567

Reaktionsgleichung

Reaktionsgleichung von HRID 275567
[PH:1](=[O:4])([OH:3])[OH:2].C(/C(/[C:14]1[N:18]=[CH:17][N:16]([C:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:15]=1)=C(\C(C)C)/C)(C)C.C[N+]1([O-])[CH2:44][CH2:43][O:42]CC1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH2:54]>C(O)(C)(C)C.O1CCCC1.O.[Os](=O)(=O)(=O)=O>[PH:1](=[O:2])([OH:4])[OH:3].[CH:20]([CH:19]([CH:26]([CH3:31])[CH3:27])[CH:43]([OH:42])[CH:44]([OH:54])[C:14]1[N:18]=[CH:17][N:16]([C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:15]=1)([CH3:25])[CH3:21]

Komponenten

7

Edukt 4

HCID 962WaterHCID 24489Sodium DithioniteHCID 82029Methyl morpholine oxideHCID 178440188HCID 178440188, Verbindung

Produkt 1

HCID 178443794HCID 178443794, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 22124471t-Butanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

A mixture of diisopropyl E-3(1-trityl-1,2,4-triazol-3-yl)prop-2-ene phosphonate (10.31 g, prepared as described in Example 15), N-methyl-morpholine N-oxide (4.69 g) and osmium tetroxide (2.5 ml, 2.5% in t-butanol) in t-butanol-tetrahydrofuran-water (10:3:1, 350 ml) was stirred at room temperature, under nitrogen, for eight hours. Sodium dithionite (10 g) and water (75 ml) were added, the mixture stirred for thirty minutes, filtered and evaporated under reduced pressure. The residue was made weakly acidic with 2M hydrochloric acid, then partitioned between ethyl acetate and brine. The aqueous layer was reextracted with ethyl acetate and the combined organic layers washed with brine, dried over magnesium sulphate and evaporated under reduced pressure. Chromatography on silica, using dichloromethane-ethanol (12:1) as eluant, gave diisopropyl (2RS,3SR)-2,3-dihydroxy-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (8.46 g, m.p. 148°-151° C.), 99% pure by GC. NMR (CDCl3): δ1.3(12H,m), 1.88-2.15(2H,m), 3.7(1 H,d), 4.13(1H,d), 4.33(1H,m), 4.6-4.8(3H,m), 7.1-7.4(15H,m), 7.95(1H,s). EI M/S: M+ 549. CI M/S: MH+ 550.

Aufarbeitung

  1. stirringthe mixture stirred for thirty minutes
  2. filtrationfiltered
  3. customevaporated under reduced pressure
  4. custompartitioned between ethyl acetate and brine
  5. washthe combined organic layers washed with brine
  6. dry with materialdried over magnesium sulphate
  7. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d169318914374fceaccd592986e99669
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05393732

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