Triethylamine → HCID 46865153, compound

HRID 879968Notes

Reaction equation

HRID 879968 reaction equation
[N:1]([CH:4]([CH2:7][NH:8][C:9]([P:11]([O:16][CH2:17][CH3:18])([O:13][CH2:14][CH3:15])=[O:12])=[O:10])[CH2:5][NH2:6])=[N+:2]=[N-:3].C(N(CC)CC)C.[O:26]([C:33]1[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CC#N>[N:1]([CH:4]([CH2:7][NH:8][C:9]([P:11]([O:16][CH2:17][CH3:18])([O:13][CH2:14][CH3:15])=[O:12])=[O:10])[CH2:5][NH:6][S:39]([C:36]1[CH:35]=[CH:34][C:33]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:38][CH:37]=1)(=[O:41])=[O:40])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27947564-Phenoxybenzene-1-sulfonyl chlorideHCID 58080260HCID 58080260, compound

Product 1

HCID 46865153HCID 46865153, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 2-azido-3-[diethylphosphonoformamido]propylamine (1.26 g, 4.5 mmol) and triethylamine (1.2 eq, 1.46 g, 5.4 mmol) in 15 ml CH3CN was added dropwise 4-phenoxybenzenesulfonyl chloride solution (1.5 eq, 68 mmol, 5.25 ml) in 15 ml CH3CN at 0° C. with stirring. After the addition, the reaction was stirred overnight at room temperature. The solvent was evaporated and the residue was purified by silica gel chromatography [eluent: DCM/1% MeOH] to yield 1.36 g (60%) a pale yellow oil.

Workup

  1. additionAfter the addition
  2. stirringthe reaction was stirred overnight at room temperature
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel chromatography [eluent: DCM/1% MeOH]

Sources & evidence

ORD record
ord-8fb521fc83d8498fa43f2cf9e1f93356
Source dataset
uspto-grants-2015_03
Patent number
US08993544B2

Reaction notes

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