Trimethyl Phosphate → HCID 474929, compound

HRID 1489515Notes

Reaction equation

HRID 1489515 reaction equation
[C:1]([NH:18][C:19]1[CH:31]=[CH:30][N:22]([C@@H:23]2[O:29][C@H:26]([CH2:27][OH:28])[CH2:25][CH2:24]2)[C:21](=[O:32])[N:20]=1)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].P(Cl)(Cl)(Cl)=O.[OH-].[Na+].C[O:41][P:42](OC)([O:44]C)=[O:43]>>[P:42]([O:28][CH2:27][C@H:26]1[O:29][C@@H:23]([N:22]2[CH:30]=[CH:31][C:19]([NH:18][C:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[N:20][C:21]2=[O:32])[CH2:24][CH2:25]1)([OH:44])([OH:43])=[O:41]

Participants

5

Reactant 4

HCID 10541Trimethyl PhosphateHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 474527HCID 474527, compound

Product 1

HCID 474929HCID 474929, compound

Conditions

Temperature
0 °C

Procedure

2.7 g (6 mmol) N4 -palmitoyl-2',3'-dideoxycytidine is added gradually to a mixture of 1.09 ml (12 mmol) phosphorylchloride and 20 ml trimethylphosphate that is stirred at 0° C. The batch is stirred for a further 2 hours when cold and then slowly neutralized with 0.5N NaOH during cooling. The precipitate that is formed is centrifuged off, absorbed in chloroform/methanol; 7/3; V/V, filtered over sodium sulphate and freed of solvent in a vacuum. The residue so obtained is crystallized several times from ethanol. When this is done, 2.5 g of N4 -palmitoyl-2',3'-dideoxycytidine-5'-phosphate is obtained and this displays an Rf value of 0.35 on the silica gel plate in the chloroform/methanol; 1/1; V/V system.

Workup

  1. stirringThe batch is stirred for a further 2 hours when cold
  2. temperatureduring cooling
  3. customThe precipitate that is formed
  4. customabsorbed in chloroform/methanol
  5. filtrationV/V, filtered over sodium sulphate
  6. customThe residue so obtained
  7. customis crystallized several times from ethanol

Sources & evidence

ORD record
ord-4d75de7a27e543479bb64fa7f0747bf2
Source dataset
uspto-grants-1997_10
Patent number
US05679652

Reaction notes

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