4-Toluenesulfonyl chloride → HCID 59526126, compound

HRID 385883Notes

Reaction equation

HRID 385883 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][C@H:6]([OH:8])[CH3:7].CCN([CH2:14][CH3:15])CC.[S:16](Cl)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17]>C(Cl)Cl>[OH:8][C@H:6]([CH3:7])[CH2:5][N:4]([S:16]([C:19]1[CH:25]=[CH:24][C:14]([CH3:15])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH2:3][CH2:2][O:1][S:16]([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 38988844(2R)-1-[(2-Hydroxyethyl)amino]propan-2-ol

Product 1

HCID 59526126HCID 59526126, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R)-1-[(2-hydroxyethyl)amino]propan-2-ol (130.0 g, 1.09 mol) in CH2Cl2 (2 L) and Et3N (304 mL, 2.18 mol) was added TsCl (305 g, 1.60 mol) portion-wise at 0° C. The mixture was maintained at room temperature overnight, then washed with water (800 mL) and brine (500 mL), dried over Na2SO4, filtered and concentrated in vacuo. The resulting residue was purified by silica gel chromatography, eluting with ethyl acetate/petroleum ether to give the title compound as a white solid.

Workup

  1. washwashed with water (800 mL) and brine (500 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by silica gel chromatography
  6. washeluting with ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-a1d83dfff5474bd498850bc0299db302
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

Loading…