Water → HCID 178443794, 화합물

HRID 582185

반응식

HRID 582185 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 178443794HCID 178443794, 화합물

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 22124471t-Butanol tetrahydrofuran water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3c1e4294f8a148a1a4518272f5658640
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05922644

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