Tributylamine → Uridine 5'-triphosphate

HRID 217097

Reaction equation

HRID 217097 reaction equation
C(N=C=NC(C)C)(C)C.[CH:10]1[C:16](=[O:17])[NH:15][C:13](=[O:14])[N:12]([C@@H:18]2[O:22][C@H:21]([CH2:23][O:24][P:25]([O:28][P:29]([O:32][P:33]([OH:36])([OH:35])=[O:34])([OH:31])=[O:30])([OH:27])=[O:26])[C@@H:20]([OH:37])[C@H:19]2[OH:38])[CH:11]=1.C(N(CCCC)CCCC)CCC.C(N(CCCC)CCCC)CCC.[Cl-].[Mg+2].[Cl-].C1C(=O)NC(=O)N([C@@H]2O[C@H](COP(OP(OP(OP(OC[C@H]3O[C@@H](N4C(=O)NC(=O)C=C4)[C@H](O)[C@@H]3O)([O-])=O)([O-])=O)([O-])=O)([O-])=O)[C@@H](O)[C@H]2O)C=1.[Na+].[Na+].[Na+].[Na+]>CN(C)C=O>[CH:10]1[C:16](=[O:17])[NH:15][C:13](=[O:14])[N:12]([C@@H:18]2[O:22][C@H:21]([CH2:23][O:24][P:25]([O:28][P:29]([O:32][P:33]([OH:35])([OH:36])=[O:34])([OH:31])=[O:30])([OH:27])=[O:26])[C@@H:20]([OH:37])[C@H:19]2[OH:38])[CH:11]=1

Participants

7

Reactant 5

HCID 7622TributylamineHCID 12734DiisopropylcarbodiimideHCID 148196Diquafosol TetrasodiumHCID 5360315Magnesium ChlorideHCID 86638271UTP tributylamine

Product 1

HCID 6133Uridine 5'-triphosphateYield 84.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Diisopropylcarbodiimide (364 μL, 2.37 mmol) was added to the dimethylformamide solution of UTP tributylamine salt prepared above in (1), and the mixture was stirred at room temperature for three hours. To the mixture were added the 0.184 M dimethylformamide solution of UMP tributylamine salt prepared above in (2) and a solution of anhydrous magnesium chloride (207.5 mg, 2.179 mmol) in dimethylformamide (4.9 mL), followed by stirring at room temperature for 255 minutes. The resultant reaction mixture was analyzed through HPLC (262 nm). As a result, Up4U (i.e., target product) was found to be produced from UTP at a synthesis yield of 84.2%.

Workup

  1. stirringby stirring at room temperature for 255 minutes
  2. customThe resultant reaction mixture

Sources & evidence

ORD record
ord-cd87aa7afee04f4884c8fb5bd24d1047
Source dataset
uspto-grants-2012_06
Patent number
US08193338B2

Linked notes

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