Water → HCID 178443794、化合物

HRID 582185

反応式

HRID 582185 の反応式
[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]

参加物

7

反応物 4

HCID 962WaterHCID 24489Sodium DithioniteHCID 82029Methyl morpholine oxideHCID 178440188HCID 178440188、化合物

生成物 1

HCID 178443794HCID 178443794、化合物

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 22124471t-Butanol tetrahydrofuran water溶媒

実験手順

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-methylmorpholine 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): δ 1.3(12H,m), 1.88-2.15(2H,m), 3.7(1H,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.

後処理

  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

出典と根拠

ORDレコード
ord-3c1e4294f8a148a1a4518272f5658640
出典データセット
uspto-grants-1999_07
特許番号
US05922644

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