Water → 6-Chloro-2-hydroxy-9-(2',3',5'-tri-O-acetyl-b-D-ribofuranosyl)purine

HRID 966384Notes

Reaction equation

HRID 966384 reaction equation
N[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:23][C@H:22]([CH2:24][O:25][C:26](=[O:28])[CH3:27])[C@@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:12]2[O:13][C:14](=[O:16])[CH3:15])=[C:4]([Cl:29])[N:3]=1.O.N(OC(C)(C)C)=[O:32]>C(O)(C)(C)C>[Cl:29][C:4]1[N:3]=[C:2]([OH:32])[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[C@@H:11]1[O:23][C@H:22]([CH2:24][O:25][C:26](=[O:28])[CH3:27])[C@@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:12]1[O:13][C:14](=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 10906Tert-Butyl nitriteHCID 10788628(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

Product 1

HCID 1784763556-Chloro-2-hydroxy-9-(2',3',5'-tri-O-acetyl-b-D-ribofuranosyl)purine

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

2-Amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (42.7 g, 100 mmoles) is dissolved in 2 liters of a tert-butyl alcohol:water mixture (1:1, v/v) with heating. After cooling the solution with an ice bath, tert-butyl nitrite (50 mL, 422 mmoles) is added in one portion. The ice bath is removed and the mixture is stirred at room temperature until gas evolution ceases (approximately 3 hours). The mixture is then frozen (dry ice/2-propanol) and lyophilized to afford the desired intermediate as a yellow solid that is used immediately or stored frozen at −20° C. without purification.

Workup

  1. temperatureAfter cooling the solution with an ice bath
  2. customThe ice bath is removed
  3. temperatureThe mixture is then frozen (dry ice/2-propanol)

Sources & evidence

ORD record
ord-2a371ac1281a455e8486de30c03d074a
Source dataset
uspto-grants-2005_10
Patent number
US06951932B2

Reaction notes

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