Sodium Hydroxide → 2',5'-Dideoxy-5-ethyl-5'-[2-(2-thienyl)acetamido]uridine

HRID 1085539

Reaction equation

HRID 1085539 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7](Cl)=[O:8].[NH2:10][CH2:11][C@H:12]1[O:16][C@@H:15]([N:17]2[CH:24]=[C:23]([CH2:25][CH3:26])[C:21](=[O:22])[NH:20][C:18]2=[O:19])[CH2:14][C@@H:13]1[OH:27].[OH-].[Na+]>O>[CH2:25]([C:23]1[C:21](=[O:22])[NH:20][C:18](=[O:19])[N:17]([CH:24]=1)[C@@H:15]1[O:16][C@H:12]([CH2:11][NH:10][C:7](=[O:8])[CH2:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[C@@H:13]([OH:27])[CH2:14]1)[CH3:26]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1623622-Thiopheneacetyl chlorideHCID 4518285'-Amino-2',5'-dideoxy-5-ethyluridine

Product 1

HCID 545708912',5'-Dideoxy-5-ethyl-5'-[2-(2-thienyl)acetamido]uridineYield 52.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.18 g of 2-thiopheneacetylchloride was added to a solution of 0.255 g of 5'-amino-2',5'-dideoxy-5-ethyluridine in 5 ml of water containing 1.2 ml of 1M sodium hydroxide solution and the resulting mixture was shaken vigorously for 10 minutes. The resulting white solid was collected by filtration, washed with water, dried at 50° C. in vacuo over phosphorus pentoxide and recrystallized from ethanol to give 0.2 g of 2',5'-dideoxy-5-ethyl-5'-[2-(2-thienyl)acetamido]uridine of melting point 215°-217° C.

Workup

  1. filtrationThe resulting white solid was collected by filtration
  2. washwashed with water
  3. dry with materialdried at 50° C. in vacuo over phosphorus pentoxide
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-4793037ff7474d6dbdda4aa7fcbe1ce1
Source dataset
uspto-grants-1991_04
Patent number
US05010060

Linked notes

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