Sodium Hydroxide → HCID 135980129, compound

HRID 2371374Notes

Reaction equation

HRID 2371374 reaction equation
[C:1]([CH2:6][N:7]1[C:24]2[C:23](=[O:25])[NH:22][C:21]([NH2:26])=[N:20][C:19]=2[N:9]([C@@H:10]2[O:18][C@H:15]([CH2:16][OH:17])[C@@H:13]([OH:14])[C@H:11]2[OH:12])[C:8]1=[O:27])([O:3]CC)=[O:2].[OH-].[Na+]>CO>[C:1]([CH2:6][N:7]1[C:24]2[C:23](=[O:25])[NH:22][C:21]([NH2:26])=[N:20][C:19]=2[N:9]([C@@H:10]2[O:18][C@H:15]([CH2:16][OH:17])[C@@H:13]([OH:14])[C@H:11]2[OH:12])[C:8]1=[O:27])([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 135500070HCID 135500070, compound

Product 1

HCID 135980129HCID 135980129, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7-carbethoxymethyl-8-oxoguanosine (1 g, 2.6 mM; Example 2), methanol (5 ml) and 1N NaOH (5 ml) was stirred at room temperature under N2 for 4 hours. Most of the methanol was removed in vacuo, and the residue was heated with water (50 ml). The solution was acidified with 1N HCl at zero degrees C to pH 5. The reaction product was purified by preparative reverse phase high performance liquid chromatography on a C-18 column (HPLC) to give the title compound as a white powder in 31 percent yield, mp above 230° C. NMR (DMSO--d6): δ10.9 (bs, 1H); 6.5 (bs, 2H) 5.6 (d, J=5Hz, 1H); 4.4 (bs, 2H). IR (KBr): 1640, 1600 and 1460 cm-1.

Workup

  1. customMost of the methanol was removed in vacuo
  2. temperaturethe residue was heated with water (50 ml)
  3. customwas acidified with 1N HCl at zero degrees C to pH 5
  4. customThe reaction product was purified by preparative reverse phase high performance liquid chromatography on a C-18 column (HPLC)

Sources & evidence

ORD record
ord-b7be6b69abc2483fa2823072084b7bc0
Source dataset
uspto-grants-1992_03
Patent number
US05093318

Reaction notes

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