HCID 86760876, compound → HCID 86760875, compound

HRID 1984954Notes

Reaction equation

HRID 1984954 reaction equation
[P:1]([O:13][CH2:14][C@H:15]1[O:19][C@@H:18]([N:20]2[CH:28]=[C:26]([CH3:27])[C:24](=[O:25])[NH:23][C:21]2=[O:22])[CH2:17][C@@H:16]1[O:29][NH:30]C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)([O:4][P:5]([O:8][P:9]([OH:12])([OH:11])=[O:10])([OH:7])=[O:6])(=[O:3])[OH:2]>N1CCCCC1.CN(C=O)C>[P:1]([O:13][CH2:14][C@H:15]1[O:19][C@@H:18]([N:20]2[CH:28]=[C:26]([CH3:27])[C:24](=[O:25])[NH:23][C:21]2=[O:22])[CH2:17][C@@H:16]1[O:29][NH2:30])([O:4][P:5]([O:8][P:9]([OH:11])([OH:12])=[O:10])([OH:7])=[O:6])(=[O:2])[OH:3]

Participants

4

Reactant 1

HCID 86760876HCID 86760876, compound

Product 1

HCID 86760875HCID 86760875, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8082PiperidineSolvent

Procedure

3′-O-(Fmoc)amino-thymidine-5′-triphosphate is dissolved in 20% piperidine in DMF (0.5 mL). The mixture is stirred at room temperature for 30 minutes and then concentrated in vacuo. The residue is redissolved in triethylammonium acetate buffer (aqueous, 10 mM; pH 7; 2 mL) and purified by rp-HPLC (C18, gradient 0-21% acetonitrile in 10 mM triethylammonium acetate over 27 minutes) to give 3′-O-amino-thymidine-5′-triphosphate as a colorless foam. The purity of the product is confirmed by analytical ion-exchange chromatography (DEAE, gradient 0-1 M triethylammonium bicarbonate in water over 30 minutes). 1H-NMR (D2O; 300 MHz): δ (ppm)=1.80 (s, 3H); 2.18 (m, 1H); 2.34-2.39 (m, 1H); 4.03-4.09 (m, 2H); 4.25 (m, 1H); 4.45 (m, 1H); 6.17 (dd, J=6.0, 9.1 Hz, 1H); 7.66 (s, 1H). 31P-NMR (D2O; 162 MHz): δ (ppm; H3PO4=0)=−14.1 (br s, IP); −16.3 (br s, IP); −27.7 (br s, 1P). MS-ESI−: [M-H]− calcd. for C10H17O14N3P3, 496.0; found, 496.4.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is redissolved in triethylammonium acetate buffer (aqueous, 10 mM; pH 7; 2 mL)
  3. custompurified by rp-HPLC (C18, gradient 0-21% acetonitrile in 10 mM triethylammonium acetate over 27 minutes)

Sources & evidence

ORD record
ord-1bc998128ca740988b5f738ef3fce179
Source dataset
uspto-grants-2009_06
Patent number
US07544794B1

Reaction notes

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