Water → HCID 178444218, compound

HRID 582179Notes

Reaction equation

HRID 582179 reaction equation
[S:1]1C=C[CH:3]=[C:2]1CC([O-])=O.[K+].[PH:11](=[O:14])([OH:13])[OH:12].[CH2:15]([C:17]([CH2:45][CH3:46])([CH:19](Br)[C:20]1[N:24]=[CH:23][N:22]([C:25]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)([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)[N:21]=1)[CH3:18])[CH3:16].[OH2:47]>O1CCCC1.C1OCCOCCOCCOCCOCCOC1>[PH:11](=[O:12])([OH:14])[OH:13].[CH2:15]([C:17]([CH2:45][CH3:46])([CH:19]([S:1][C:2](=[O:47])[CH3:3])[C:20]1[N:24]=[CH:23][N:22]([C:25]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)([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)[N:21]=1)[CH3:18])[CH3:16]

Participants

6

Reactant 3

HCID 962WaterHCID 23696799Potassium 2-thienylacetateHCID 178442503HCID 178442503, compound

Product 1

HCID 178444218HCID 178444218, compound

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 18-crown-6 (0.04 g) in dry tetrahydrofuran (25 ml) was treated successively with potassium thiolacetate (0.59 g) and diethyl 3-bromo-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (1.94 g, prepared as described in Example 29). The mixture was allowed to stand for two days, poured into water and extracted with ethyl acetate. The extracts were washed with brine, dried over magnesium sulphate and evaporated under reduced pressure. The residue was chromatographed on silica, using dichloromethane-ethanol (49:1) as eluant, to give diethyl 3-acetylthio-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (1.51 g) as a pale yellow oil. NMR(CDCl3): δ 1.3(6H,m), 1.6-1.9(2H,m), 2.2-2.3(2H,m), 2.4(3H,s), 4.0(4H,m), 4.9(1H,t), 7.15(6H,m), 7.3(9H,m), 7.9(1H,s), M/S: M+ 563.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-f05897474ccc466886388844610f39bc
Source dataset
uspto-grants-1999_07
Patent number
US05922644

Reaction notes

Loading…