Triethylene Glycol → 2-(2-(2-Azidoethoxy)ethoxy)ethanol

HRID 2390606Notes

Reaction equation

HRID 2390606 reaction equation
FC(F)(F)C([NH:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][OH:14])=O.C(O)COCCOCCO.[N-:27]=[N+:28]=[N-]>CO.[Pd]>[N:5]([CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][OH:14])=[N+:27]=[N-:28]

Participants

6

Reactant 3

HCID 8172Triethylene GlycolHCID 33558AzideHCID 577571468-Trifluoroacetamido-3,6-dioxa-1-octanol

Product 1

HCID 110084382-(2-(2-Azidoethoxy)ethoxy)ethanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

8-Trifluoroacetamido-3,6-dioxa-1-octanol (1f: 8-azido-3,6-dioxa-1-octanol (Amvamzollo, P. H.; Sinay, P. Carbohydr. Res. 1986, 150, 199-212) (0.7 g, 4.0 mmol) was synthesized from triethylene glycol following the reported procedure (Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1991, 56, 4326-4329). The azide was combined with Pd/C (150 mg) in MeOH (8.0 mL) and stirred 12 h under H2 (1 atm). The suspension was filtered over celite, and the filtrate was concentrated to afford the amine (0.590 g, 4.0 mmol) in quantitative yields (Sato, H.; Hayashi, E.; Yamada, N.; Yatagai, M.; Takahara, Y. Bioconjugate Chem. 2001, 12, 701-710.). Following general procedure 1, 2-[2-(2-aminoethoxy)ethoxy]ethanol (0.590 g, 3.95 mmol) was combined with triethylamine (1.378 mL, 9.89 mmol) and trifluoroacetic anhydride (0.782 mL, 5.54 mmol) in MeOH (5 mL). Purification by silica gel chromatography (EtOAc) yielded 0.576 g (60%) of if as a white solid. 1H (300 MHz, CD3OD): δ 7.87 (br s, 1H), 3.73 (m, 2H), 3.68-3.60 (m, 10H), 3.55 (t, 2H, J=4.5 Hz), 3.32 (br s, 1H); 13C (75 mHz, CD3OD): δ 157.6 (q, J=36.6 Hz), 116.1 (q, J=286.1 Hz), 72.68, 70.35, 70.24, 68.90, 61.52, 39.84; ESI-MS calcd for C8H14F3NO4 [M−H]−: 244.0797. found 244.0795.

Workup

  1. filtrationThe suspension was filtered over celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-df7bc11e06524988890127080f3e1f85
Source dataset
uspto-grants-2012_09
Patent number
US08273778B2

Reaction notes

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