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

HRID 966386Notes

Reaction equation

HRID 966386 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.N(OC(C)(C)C)=[O:31]>CC(O)C.O>[Cl:29][C:4]1[N:3]=[C:2]([OH:31])[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 2

HCID 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 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A suspension of 2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (291.2 g, 0.68 mol, Example 1, Step B) in 2-propanol and water (1:1, 15,560 mL) which was heated to achieve homogeneity. The solution was cooled to <15° C. and then t-butyl nitrite (357 mL, 3.0 mol) was added. The reaction was allowed to warm to room temperature and stirred until the evolution of gas subsided. The reaction was partitioned between ethyl acetate (7,300 mL) and water and the phases allowed to separate. The aqueous layer was further extracted with ethyl acetate (2×7,300 mL) and the combined organic layers were dried over magnesium sulfate, filtered and removed under reduced pressure to yield a viscous oil. Typical Yield: Quantitative.

Workup

  1. temperaturewas heated
  2. temperatureThe solution was cooled to <15° C.
  3. customThe reaction was partitioned between ethyl acetate (7,300 mL) and water
  4. customto separate
  5. extractionThe aqueous layer was further extracted with ethyl acetate (2×7,300 mL)
  6. dry with materialthe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. customremoved under reduced pressure
  9. customto yield a viscous oil

Sources & evidence

ORD record
ord-9f4a03e0ed994fb6a7b4f73e72f6ddd9
Source dataset
uspto-grants-2005_10
Patent number
US06951932B2

Reaction notes

Loading…