((2S,4R)-4-acetoxy-5-(2-amino-6-methoxy-9H-purin-9-yl)-4-methyl-tetrahydrofuran-2-yl)methyl benzoate → (3R,5S)-2-(2-amino-6-methoxy-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3-ol

HRID 409012Notes

Reaction equation

HRID 409012 reaction equation
C([O:9][CH2:10][C@@H:11]1[CH2:15][C@:14]([O:17]C(=O)C)([CH3:16])[CH:13]([N:21]2[CH:29]=[N:28][C:27]3[C:22]2=[N:23][C:24]([NH2:32])=[N:25][C:26]=3[O:30][CH3:31])[O:12]1)(=O)C1C=CC=CC=1>N>[NH2:32][C:24]1[N:23]=[C:22]2[C:27]([N:28]=[CH:29][N:21]2[CH:13]2[C@:14]([CH3:16])([OH:17])[CH2:15][C@@H:11]([CH2:10][OH:9])[O:12]2)=[C:26]([O:30][CH3:31])[N:25]=1

Participants

3

Reactant 1

HCID 66778608((2S,4R)-4-acetoxy-5-(2-amino-6-methoxy-9H-purin-9-yl)-4-methyl-tetrahydrofuran-2-yl)methyl benzoate

Product 1

HCID 66778804(3R,5S)-2-(2-amino-6-methoxy-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3-olYield 79%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

Methanolic ammonia (7N, 20 mL) was added to ((2S,4R)-4-acetoxy-5-(2-amino-6-methoxy-9H-purin-9-yl)-4-methyl-tetrahydrofuran-2-yl)methyl benzoate (from step 11) (1.53 g) and stirred at room temperature for 24 h in a sealed tube. The volatiles were evaporated under vacuum and the resulting residue was loaded directly on to the column and eluted with CH2Cl2/MeOH (10:1) as a gradient mixture to give 0.802 g of compound (79% yield). mp: 140° C.-142° C.

Workup

  1. customThe volatiles were evaporated under vacuum
  2. washeluted with CH2Cl2/MeOH (10:1) as a gradient mixture

Sources & evidence

ORD record
ord-538a4428ab934f9db25976804702c3e1
Source dataset
uspto-grants-2014_06
Patent number
US08759318B2

Reaction notes

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