Pyridine → HCID 44475518, compound

HRID 537642Notes

Reaction equation

HRID 537642 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-c7683621d5ae4f5abf0e97243081129c
Source dataset
uspto-grants-2014_10
Patent number
US08865122B2

Reaction notes

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