Perfluorophenyl acetate → HCID 23541117, compound

HRID 1793260Notes

Reaction equation

HRID 1793260 reaction equation
[NH2:1][CH2:2][C@:3]1([CH2:17][OH:18])[O:7][C@@H:6]([N:8]2[CH:15]=[CH:14][C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:16].[C:19](OC1C(F)=C(F)C(F)=C(F)C=1F)(=[O:21])[CH3:20]>CN(C)C=O>[C:19]([NH:1][CH2:2][C@:3]1([CH2:17][OH:18])[O:7][C@@H:6]([N:8]2[CH:15]=[CH:14][C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:16])(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 87968Perfluorophenyl acetateHCID 23541118HCID 23541118, compound

Product 1

HCID 23541117HCID 23541117, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4′-C-Aminomethyl-2′-deoxyuridine (13) (0.034 g, 0.13 mmol) was dissolved in anhydrous N,N-dimethylformamide (0.5 mL) at ambient temperature. Excess pentafluorophenyl acetate (0.88 g, 0.39 mmol) was then added directly to the reaction mixture as a solid. The resulting solution was stirred for 18 hours at ambient temperature. The solvent was then removed under vacuum and the residue re-dissolved in water and then washed with toluene. The aqueous layer was then separated and the solvent removed under vacuum. The title compound was obtained as an amorphous solid (0.032 g, 82%). δH(300 MHz, D2O) 7.68(1H, d, H-6), 6.11(1H, dd, H-1′), 5.71(1H, d, H-5), 4.44(1H, dd, H-3′), 4.49(2H, 2d, H-5′), 3.33(2H, 2d, 4′-C—CH2), 2.33(2H, m, H-2′), 1.89(3H, s, CH3CONH); δC(75.45 MHz, D2O) 175.60, 167.08, 152.43, 142.86, 102.93, 88.93, 85.57, 71.91, 63.16, 40.37, 39.15, 22.72; ES +ve m/z 300(M+H)+, 242(M−CH3CONH)+.

Workup

  1. customThe solvent was then removed under vacuum
  2. dissolutionthe residue re-dissolved in water
  3. washwashed with toluene
  4. customThe aqueous layer was then separated
  5. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-8ed602aad6f84b358ab5d4461855826e
Source dataset
uspto-grants-2006_07
Patent number
US07078499B2

Reaction notes

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