Isoamylamine → 2-Hydroxy-3-[(3-methylbutyl)amino]propane-1-sulfonic acid

HRID 239806Notes

Reaction equation

HRID 239806 reaction equation
[CH2:1]([NH2:6])[CH2:2][CH:3]([CH3:5])[CH3:4].Cl[CH2:8][CH:9]([OH:15])[CH2:10][S:11]([OH:14])(=[O:13])=[O:12].[Na]>O1CCOCC1.O>[OH:15][CH:9]([CH2:8][NH:6][CH2:1][CH2:2][CH:3]([CH3:5])[CH3:4])[CH2:10][S:11]([OH:14])(=[O:13])=[O:12]

Participants

6

Reactant 3

HCID 7894IsoamylamineHCID 313603-Chloro-2-hydroxypropane-1-sulfonic acidHCID 5360545Sodium

Product 1

HCID 589318312-Hydroxy-3-[(3-methylbutyl)amino]propane-1-sulfonic acidYield 27%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a 80° C. solution of isoamylamine (2.0 g, 22.9 mmol) in 1,4-dioxane (9 mL) and water (3 mL) was added via syringe pump (1 h addition) a solution of 3-chloro-2-hydroxy-propane sulfonic acid, sodium salt (3.04 g, 15.3 mmol) in 1,4-dioxane (9.5 mL) and water (0.5 mL). The solution was stirred overnight at 80° C. The solvent was evaporated. The product was passed through an ion exchange column (Dowex 50×8, 100 g, solvent: water). It was recrystallized in absolute EtOH and lyophilized. Yield: 27%. 1H NMR (H2O, 500 MHz) δ ppm 4.24 (m, 1H), 3.22 (m, 1H), 3.02 (m, 5H), 1.49 (m, 3H), 0.79 (d, 3H, J=6.3 Hz). 13C(H2O, 125 MHz) δ ppm 63.54, 54.89, 51.53, 46.48, 34.12, 25.46, 21.56, 21.46. ES-MS 226 (M+1).

Workup

  1. customThe solvent was evaporated
  2. customIt was recrystallized in absolute EtOH

Sources & evidence

ORD record
ord-16e1a49a93764f2086e954a54814690f
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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