Sodium Methoxide → HCID 53671578, compound

HRID 232380Notes

Reaction equation

HRID 232380 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][C@H:8]1[O:12][C@@H:11]([N:13]2[CH:20]=[C:19]([CH2:21][CH3:22])[C:17](=[O:18])[NH:16][C:14]2=[O:15])[CH2:10][C@@H:9]1[O:23]C(=O)C)(=O)C.C[O-].[Na+]>CO>[CH2:21]([C:19]1[C:17](=[O:18])[NH:16][C:14](=[O:15])[N:13]([CH:20]=1)[C@@H:11]1[O:12][C@H:8]([CH2:7][CH2:6][CH2:5][OH:4])[C@@H:9]([OH:23])[CH2:10]1)[CH3:22]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18633454HCID 18633454, compound

Product 1

HCID 53671578HCID 53671578, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.10 g of 5'-(2-acetoxyethyl)-3'-O-acetyl-2',5'-dideoxy-5-ethyluridine was treated with 5 ml of a dilute solution of sodium methoxide in methanol. After standing at room temperature for 2 hours the solution was neutralized by the addition of a cross-linked polystyrene-divinylbenzene cation exchange resin containing sulfonic acid groups (H+ form) and then filtered. The filtrate was evaporated to dryness to give 0.045 g of 2',5'-dideoxy-5-ethyl-5'-(2-hydroxyethyl)uridine in the form of a white solid of melting point 113°-115° C.

Workup

  1. additioncontaining sulfonic acid groups (H+ form)
  2. filtrationfiltered
  3. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-535ad4219f7c44378b5ec54b7f95db91
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

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