Water → HCID 58078852, compound

HRID 535279Notes

Reaction equation

HRID 535279 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+]=[N-].[C:28]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:33]=CC=C[CH:29]=1.O>C1COCC1>[CH2:4]([NH2:1])[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:27][CH2:33][C:28]#[CH:29]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 10960238O-(2-Azidoethyl)heptaethylene glycol

Product 1

HCID 58078852HCID 58078852, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

23-Azido-3,6,9,12,15,18,21-heptaoxatricosan-1-ol (azido-PEG8-yne) (960 mg, 2.52 mmol, 1 equiv.), triphenylphosphine (992 mg, 3.78 mmol, 1.5 equiv.), and water (68 μL, 3.78 mmol, 1.5 equiv.) were dissolved in THF (10 mL) and stirred for 12 h. Reaction was concentrated and chromatographed (3 cm×20 cm Silica, CH2Cl2 then ramp to 80:20:1 CH2Cl2:MeOH:Et3N) and concentrated to yield 3,6,9,12,15,18,21,24-octaoxaheptacos-26-yn-1-amine (9) as a clear oil (815 mg, 91% yield). IR (thin film, NaCl) 3105 (br), 2914 (m), 1781 (m), 1638 (m), 1169 (s) cm−1. 1H-NMR (500 MHz, CDCl3) δ 4.17 (d, 2H, J=2.4), 3.66-3.57 (m, 28H), 3.54 (t, 2H, J=5.3 Hz), 2.88 (t, 2H, J=5.0 Hz), 2.41 (t, 1H, J=2.4 Hz), 2.18 (br s, 2H). 13C NMR (125 MHz, CDCl3) δ 79.52, 74.59, 72.54, 70.41, 70.38, 70.38, 70.35, 70.31, 70.20, 70.06, 68.90, 58.20, 41.44. HRMS (ES+) calc'd for C19H37NO8 (M+H) m/z 408.259194. Found 408.25712.

Workup

  1. customReaction
  2. concentrationwas concentrated
  3. customchromatographed (3 cm×20 cm Silica, CH2Cl2
  4. concentrationMeOH:Et3N) and concentrated

Sources & evidence

ORD record
ord-0ffeae56908d42abb476c23b471df72a
Source dataset
uspto-grants-2014_10
Patent number
US08859509B2

Reaction notes

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