Triethylamine → HCID 178442503, compound

HRID 582173Notes

Reaction equation

HRID 582173 reaction equation
[Br:1]Br.C(P(CCCC)CCCC)CCC.[PH:16](=[O:19])([OH:18])[OH:17].[CH2:20]([C:22]([CH2:50][CH3:51])([CH:24](O)[C:25]1[N:29]=[CH:28][N:27]([C:30]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:26]=1)[CH3:23])[CH3:21].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[PH:16](=[O:17])([OH:19])[OH:18].[CH2:20]([C:22]([CH2:50][CH3:51])([CH:24]([Br:1])[C:25]1[N:29]=[CH:28][N:27]([C:30]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:26]=1)[CH3:23])[CH3:21]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 13831TributylphosphineHCID 24408BromineHCID 178444075HCID 178444075, compound

Product 1

HCID 178442503HCID 178442503, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of bromine (0.53 g) in dichloromethane (1 ml) was added dropwise to a solution of tri-n-butylphosphine (0.68 g) in dichloromethane (12 ml), whilst maintaining the temperature below 0° C. The mixture was stirred for ten minutes at this temperature then treated, dropwise with stirring, with a solution of diethyl 3-hydroxy-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (1.5 g, prepared as described in Example 24) and triethylamine (0.30 g) in dichloromethane (20 ml), maintaining the temperature below 0° C. It was allowed to warm slowly to room temperature, to stand for two days, then diluted with ethyl acetate, washed with water and 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-bromo-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (1.27 g, m.p. 108-110° C.). NMR (CDCl3): δ 1.13(6H,dt), 1.6-2.1(2H,m), 2.5-2.6(2H,m), 4.1(4H,m), 5.15(1H,t), 7.1(6H,m), 7.3(9H,m), 7.9(1H,s). M/S: M+ 567,569.

Workup

  1. temperaturewhilst maintaining the temperature below 0° C
  2. additionthen treated
  3. temperaturemaintaining the temperature below 0° C
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated under reduced pressure
  7. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-5817be4a888b40d09512a664c4442e5d
Source dataset
uspto-grants-1999_07
Patent number
US05922644

Reaction notes

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