Water → H2N-PEG4-Propyne

HRID 709925Notes

Reaction equation

HRID 709925 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][C:17]#[CH:18])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(Cl)Cl.CO>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][C:17]#[CH:18]

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 21226129Dichloromethane methanolHCID 86672682HCID 86672682, compound

Product 1

HCID 86580391H2N-PEG4-PropyneYield 85.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-azido-3,6,9,12-tetraoxapentadec-14-yne 6 (2.45 g, 9.53 mmol, 1 equiv.), triphenylphosphine (3.00 g, 11.4 mmol, 1.2 equiv.), and water (172 mL, 9.53 mmol, 1.0 equiv.) were dissolved in THF (30 mL) and stirred for 12 h when TLC (95:5 CH2Cl2/CH3OH) indicated completion. Reaction was concentrated and chromatographed (100% CH2Cl2 to 80:20:1 CH2Cl2/MeOH/Et3N) to yield 7 as a clear oil (1.88 g, 85% yield). IR (thin film, NaCl) 3372 (br), 3251 (s), 2868 (s), 2112 (w), 1652 (m), 1596 (m), 1459 (m), 1350 (m), 1301 (m), 1249 (m), 1100 (s), 946 (m), 681 (m) cm−1. 1H-NMR (500 MHz, CDCl3) δ 4.16 (m, 2H), 3.66-3.57 (m, 12H), 3.49 (t, 2H, J=5.3 Hz), 2.85 (t, 2H, J=5.0 Hz), 2.56 (bs, 2H), 2.41 (m, 1H). 13C NMR (125 MHz, CDCl3) δ 79.52, 74.63, 73.06, 70.45, 70.41, 70.24, 70.11, 68.96, 58.26, 41.50. HRMS (ES+) calc'd for C11H21NO4 (M+H) m/z 232.154335. Found 232.15402.

Workup

  1. customReaction
  2. concentrationwas concentrated
  3. customchromatographed (100% CH2Cl2 to 80:20:1 CH2Cl2/MeOH/Et3N)

Sources & evidence

ORD record
ord-9fd4a4130b2045c19caed83ea7afa216
Source dataset
uspto-grants-2015_11
Patent number
US09181224B2

Reaction notes

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