(Diethylamino)sulfur trifluoride → HCID 44475673, compound

HRID 2088264Notes

Reaction equation

HRID 2088264 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]O)=[N+:2]=[N-:3].CCN(S(F)(F)[F:34])CC>C(Cl)Cl>[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][F:34])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 10960238O-(2-Azidoethyl)heptaethylene glycol

Product 1

HCID 44475673HCID 44475673, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

23-Azido-3,6,9,12,15,18,21-heptaoxatricosan-1-ol (500 mg, 1.26 mmol) was dissolved in DCM (2 mL) and cooled to −10° C. DAST (482 μL, 3.78 mmol) was added in portions to the cooled solution and the resulting mixture was stirred at −10° C. for 30 minutes then allowed to warm to room temperature and stirred for additional 20 hours. The excess of DAST was quenched with methanol (5 mL) and the solvents were subsequently evaporated at the reduced pressure. The oily residue was dissolved in the water (3 mL) and the pH was adjusted to 5 using NaHCO3. The crude product was purified on semipreparative HPLC (System E) to yield 122 mg (24%) of 4 as a yellowish oil. 1H NMR (500 MHz, CDCl3): δ 3.39 (t, J=5.0 Hz, 2H), 3.65-3.68 (m, 26H), 3.75 (dt, J=4.2 Hz, 29.6 Hz, 2H), 4.56 (dt, J=4.0 Hz, 47.5 Hz, 2H); 13C NMR (125.7 MHz, CDCl3): δ 50.8, 70.1, 70.4, 70.5, 70.7-70.8, 70.9, 83.2 (d, J=169 Hz); 19F NMR (470.6 MHz, CDCl3): 6-225.9; MS ESI (m/z): [M+H]+ calcd. for C16H33FO7N3, 398.2; found 398.0.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for additional 20 hours
  3. customThe excess of DAST was quenched with methanol (5 mL)
  4. customthe solvents were subsequently evaporated at the reduced pressure
  5. dissolutionThe oily residue was dissolved in the water (3 mL)
  6. customThe crude product was purified on semipreparative HPLC (System E)

Sources & evidence

ORD record
ord-1495cf922ee14ef9ab2f1bcfd7edae27
Source dataset
uspto-grants-2013_05
Patent number
US08435488B2

Reaction notes

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