Reaction #2175445

Reaction equation

23-azido-3,6,9,12,15,18,21-heptaoxatricosan-1-ol

toluenesulfonyl chloride

pyridine

pyridine

→

3

Yield 25.0%

23-azido-3,6,9,12,15,18,21-heptaoxatricos-1-yl p-toluenesulfonate

Yield 25.0%

Conditions

Workup

1. 1
   OtherThe solvent was evaporated
2. 2
   Otherthe crude product was purified on SiO2 column
3. 3
   Otherpurified on semipreparative HPLC (System E)

Procedure

A solution of 23-azido-3,6,9,12,15,18,21-heptaoxatricosan-1-ol (800 mg, 2.02 mmol) in pyridine (4 mL) was added dropwise to the solution of toluenesulfonyl chloride (771 mg, 4.04 mmol) and 4-dimethylaminopyridine (100 mg) in pyridine (10 mL) at room temperature. The mixture was stirred for 24 hours at room temperature. The solvent was evaporated and the crude product was purified on SiO2 column using hexanes/ethylacetate gradient 0-100% followed by ethylacetate/methanol gradient 0-100%, then purified on semipreparative HPLC (System E) to yield 280 mg (25%) of 3 as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 2.45 (s, 3H), 3.38 (t, J=5.02 Hz, 2H), 3.58-3.70 (m, 28H), 4.16 (t, J=5.00 Hz, 2H), 7.34 (d, J=8.4 Hz, 2H), 7.80 (d, J=8.4 Hz, 2H); 13C NMR (100.6 MHz, CDCl3): δ 21.6, 50.7, 68.7, 69.2, 70.0, 70.5-70.8, 128.0, 129.7, 133.1, 144.7; MS ESI (m/z): [M+H]+ calcd. for C23H39N3O10S 549.24; found 549.9.

Source