Uridine Monophosphate → Uridine

HRID 430599

Reaction equation

HRID 430599 reaction equation
P([O:5][CH2:6][C@H:7]1[O:11][C@@H:10]([N:12]2[CH:19]=[CH:18][C:16](=[O:17])[NH:15][C:13]2=[O:14])[C@H:9]([OH:20])[C@@H:8]1[OH:21])(O)(O)=O.[CH2:22](N(CCCC)CCCC)[CH2:23][CH2:24]C.[CH2:35](N(CCCC)CCCC)CCC.P(OC[C@H]1O[C@@H](N2C=CC(=O)NC2=O)[C@H](O)[C@@H]1O)(O)(O)=O.C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(CCCC)CCCC)CCC.P(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O)(OP(OP(O)(O)=O)(O)=O)(=O)O.C1C(N=NC2C(=O)N(C3C=CC(S([O-])(=O)=O)=CC=3)N=C2C([O-])=O)=CC=C(S([O-])(=O)=O)C=1.[Na+].[Na+].[Na+]>CN(C=O)C>[C@@H:10]1([N:12]2[CH:19]=[CH:18][C:16](=[O:17])[NH:15][C:13]2=[O:14])[O:11][C@H:7]([CH2:6][OH:5])[C@@H:8]([OH:21])[C@H:9]1[OH:20].[CH2:19]([N:12]([CH2:10][CH2:9][CH2:8][CH3:7])[CH2:13][CH2:22][CH2:23][CH3:24])[CH2:18][CH2:16][CH3:35]

Participants

9

Reactant 6

HCID 6030Uridine MonophosphateHCID 7622Tributylamine2×HCID 682631,1'-CarbonyldiimidazoleHCID 164825TartrazineHCID 14561855Uridine 5'-monophosphate tributylamine saltHCID 86757612Cytidine 5'-triphosphate tributylamine salt

Product 2

HCID 6029UridineHCID 7622Tributylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent4×

Conditions

Temperature
25 °C

Procedure

Uridine 5′-monosphate, tributylamine salt was prepared by dissolving uridine 5′-monophosphate, free acid (Sigma) (3.0 g) with tributylamine (2.0 mL) in DMF to make a 0.34M solution. An anhydrous DMF solution of uridine 5′-monophosphate tributylamine salt (5.6 ml, 1.89 mmol, 0.34 M) was added to a 10 ml round bottomed flask under N2 and carbonyldiimidazole (459 mg, 2.83 mmol) was added and the solution stirred at 25° C. for 30 min. A DMF solution of cytidine 5′-triphosphate tributylamine salt, prepared by treating the trisodium salt with Dowex 50H+ resin followed by tributylamine in DMF was added and the reaction mixture stirred at 65° C. for 3 h. The solution was evaporated in vacuo and purified two times by column chromatography (DEAE Sephadex; H2O→0.3M NH4HCO3 gradient). The pure fractions were concentrated in vacuo at 35° C., and H2O added and reevaporated ten times to obtain a white solid (203 mg): 1H NMR (D2O, TMS) δ4.1 (m, br, 6H), 4.2 (m, 4H), 5.8 (m, 3H), 5.95 (m, 1H), 7.7 (m, 2H); 31P NMR (D2O, H3PO4 std) δ−22.4 (m, 2P), −10.6 (m, 2P); Exact mass calc for C18H26N5O22P4 (M−H)=788.0020, found 787.9985.

Workup

  1. additionwas added
  2. stirringthe reaction mixture stirred at 65° C. for 3 h
  3. customThe solution was evaporated in vacuo
  4. custompurified two times by column chromatography (DEAE Sephadex; H2O→0.3M NH4HCO3 gradient)
  5. concentrationThe pure fractions were concentrated in vacuo at 35° C.
  6. additionH2O added
  7. customreevaporated ten times

Sources & evidence

ORD record
ord-75de3408bb1a4e3b80f7f0dd9f6dbefa
Source dataset
uspto-grants-2001_11
Patent number
US06323187B1

Linked notes

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