Carbon Disulfide → 2-Thioadenosine

HRID 1729615Notes

Reaction equation

HRID 1729615 reaction equation
C(O[N:9]=[C:10]([C:12]1[N:13]=[CH:14][N:15]([C@@H:18]2[O:30][C@H:29]([CH2:31][O:32]C(=O)C)[C@@H:24]([O:25]C(=O)C)[C@H:19]2[O:20]C(=O)C)[C:16]=1[NH2:17])[NH2:11])C1C=CC=CC=1.[C:36](=S)=[S:37]>[OH-].[Na+].CO>[CH:14]1[N:15]([C@@H:18]2[O:30][C@H:29]([CH2:31][OH:32])[C@@H:24]([OH:25])[C@H:19]2[OH:20])[C:16]2[C:12](=[C:10]([NH2:11])[NH:9][C:36]([N:17]=2)=[S:37])[N:13]=1

Participants

5

Reactant 2

HCID 6348Carbon DisulfideHCID 131710513HCID 131710513, compound

Product 1

HCID 64519652-ThioadenosineYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

0.45 g of 5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carboxamide O-benzyl-oxime was dissolved in a mixture of 0.30 g of sodium hydroxide, 5 ml of methanol and 0.5 ml of carbon disulfide, and the resulting mixture was allowed to react in an autoclave at 170° C for 4 hours under autogenous pressure (about 12 - 13 Kg/cm2). The reaction product was worked up in the same manner as described in Example 7 to obtain 0.265 g of 2-thioadenosine having a melting point of 198° C (with decomposition) in a 91% yield.

Workup

  1. customto react in an autoclave at 170° C for 4 hours under autogenous pressure (about 12 - 13 Kg/cm2)

Sources & evidence

ORD record
ord-829afe5eb6814dec80e38cd6fb606b1e
Source dataset
uspto-grants-1976_11
Patent number
US03989682

Reaction notes

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