Ammonium → 2-Thioadenosine

HRID 1729617Notes

Reaction equation

HRID 1729617 reaction equation
O.[C@@H:2]1([N:11]2[C:20]3[C:14](=[C:15]([N+:17]([O-])=[CH:18][N:19]=3)[NH2:16])[N:13]=[CH:12]2)[O:10][C@H:7]([CH2:8][OH:9])[C@@H:5]([OH:6])[C@H:3]1[OH:4].[OH-].[Na+].[NH4+].CN(C)C=O.C(=S)=[S:31]>C(N(CC)CC)C>[CH:12]1[N:11]([C@@H:2]2[O:10][C@H:7]([CH2:8][OH:9])[C@@H:5]([OH:6])[C@H:3]2[OH:4])[C:20]2[C:14](=[C:15]([NH2:16])[NH:17][C:18]([N:19]=2)=[S:31])[N:13]=1

Participants

7

Reactant 5

HCID 223AmmoniumHCID 6228DimethylformamideHCID 6348Carbon DisulfideHCID 14798Sodium HydroxideHCID 178507182HCID 178507182, compound

Product 1

HCID 64519652-ThioadenosineYield 98%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In the same manner as described in Example 11, 9.6 g of adenosine 1-oxide monohydrate was treated with a 5N sodium hydroxide aqueous solution and Diaion SK-1B (ammonium-type). 60 ml of N,N-dimethylformamide and 60 ml of triethylamine were added to the resulting residue to form a solution, and 30 ml of carbon disulfide was then added to the solution. The resulting mixture was allowed to react in an autoclave at 130° C for 4 hours under autogenous pressure (about 10 kg/cm2). The reaction mixture was concentrated to dryness followed by working up in the same manner as described in Example 11 to obtain 9.35 g of 2-thioadenosine as crystals having a melting point of 198° C (with decomposition) in a 98% yield.

Workup

  1. additionwas then added to the solution
  2. customto react in an autoclave at 130° C for 4 hours under autogenous pressure (about 10 kg/cm2)
  3. concentrationThe reaction mixture was concentrated to dryness

Sources & evidence

ORD record
ord-3336e4cc7df34c99b81cf5e54bd219fc
Source dataset
uspto-grants-1976_11
Patent number
US03989682

Reaction notes

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