Pyridine → HCID 44475518, compound

HRID 2088263Notes

Reaction equation

HRID 2088263 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][OH:27])=[N+:2]=[N-:3].[C:28]1(C)[C:29]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:31]=[CH:32][CH:33]=1.N1C=CC=C[CH:40]=1>CN(C)C1C=CN=CC=1>[C:32]1([CH3:40])[CH:33]=[CH:28][C:29]([S:34]([O:27][CH2:26][CH2:25][O:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][O:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])(=[O:35])=[O:36])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 8623o-Toluenesulfonyl chlorideHCID 10960238O-(2-Azidoethyl)heptaethylene glycol

Product 1

HCID 44475518HCID 44475518, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

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.

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified on SiO2 column
  3. custompurified on semipreparative HPLC (System E)

Sources & evidence

ORD record
ord-d0bd5ae415fb49bf9039f39811c03c13
Source dataset
uspto-grants-2013_05
Patent number
US08435488B2

Reaction notes

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