Tris(2-carboxyethyl)phosphine hydrochloride → 4-{2-[(2-Mercapto-2-methylpropyl)(methyl)amino]ethoxy}-2,6-bis(hydroxymethyl)pyridine

HRID 446646Notes

Reaction equation

HRID 446646 reaction equation
Cl.C(CCP(CCC(O)=O)CCC(O)=O)(O)=O.[CH3:18][N:19]([CH2:33][C:34]([CH3:39])([S:36]SC)[CH3:35])[CH2:20][CH2:21][O:22][C:23]1[CH:28]=[C:27]([CH2:29][OH:30])[N:26]=[C:25]([CH2:31][OH:32])[CH:24]=1>O.CO>[SH:36][C:34]([CH3:39])([CH3:35])[CH2:33][N:19]([CH3:18])[CH2:20][CH2:21][O:22][C:23]1[CH:24]=[C:25]([CH2:31][OH:32])[N:26]=[C:27]([CH2:29][OH:30])[CH:28]=1

Participants

5

Reactant 2

HCID 2734570Tris(2-carboxyethyl)phosphine hydrochlorideHCID 575709534-{2-[Methyl(2-methyl-2-(methyldisulphanyl)propyl)amino]ethoxy)-2,6-bis(hydroxymethyl)pyridine

Product 1

HCID 866712894-{2-[(2-Mercapto-2-methylpropyl)(methyl)amino]ethoxy}-2,6-bis(hydroxymethyl)pyridineYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 198 mg of tris(2-carboxyethyl)phosphine hydrochloride in 730 μl of water is added to 80 mg of 4-{2-[methyl(2-methyl-2-(methyldisulphanyl)propyl)amino]ethoxy}-2,6-bis(hydroxymethyl)pyridine in solution in 1.95 ml of methanol. After 2 h at AT, the mixture is concentrated under RP and the residue is taken up in 10 ml of water. The aqueous phase is brought to pH=8 by addition of an aqueous sodium hydroxide solution and then extracted 2× with AcOEt. The combined organic phases are washed with a saturated aqueous NaCl solution and concentrated under RP. 68 mg of 4-{2-[(2-mercapto-2-methylpropyl)(methyl)amino]ethoxy}-2,6-bis(hydroxymethyl)pyridine are obtained.

Workup

  1. concentrationthe mixture is concentrated under RP
  2. additionThe aqueous phase is brought to pH=8 by addition of an aqueous sodium hydroxide solution
  3. extractionextracted 2× with AcOEt
  4. washThe combined organic phases are washed with a saturated aqueous NaCl solution
  5. concentrationconcentrated under RP

Sources & evidence

ORD record
ord-b9bf20f70c8249c9a6e8e81a29e9bea2
Source dataset
uspto-grants-2013_07
Patent number
US08481042B2

Reaction notes

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