Imidazole → HCID 15817419, compound

HRID 129954Notes

Reaction equation

HRID 129954 reaction equation
[N:1]([CH2:4][C@H:5]1[O:9][C@@H:8]([N:10]2[C:27]3[N:26]=[CH:25][N:24]=[C:14]([NH:15][C:16](=[O:23])[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:13]=3[N:12]=[CH:11]2)[CH2:7][C@@H:6]1[OH:28])=[N+:2]=[N-:3].[Si:29](Cl)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30].N1C=CN=C1>CN(C)C=O>[N:1]([CH2:4][C@H:5]1[O:9][C@@H:8]([N:10]2[C:27]3[N:26]=[CH:25][N:24]=[C:14]([NH:15][C:16](=[O:23])[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:13]=3[N:12]=[CH:11]2)[CH2:7][C@@H:6]1[O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 11383419HCID 11383419, compound

Product 1

HCID 15817419HCID 15817419, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8.9 g (24 mmol) of 5'-Azido-N6-benzoyl-2',5'-dideoxyadenosine (which can be prepared as in reference 36), 5.4 g (35 mmol) of t-butyldimethylsilyl chloride, and 3.3 g (48 mmol) of imidazole in 100 ml of anhydrous dimethylformamide (DMF) was stirred at room temperature (RT) for 20 hr. The solvent was removed under vacuum, and the residue was partitioned between one half saturated brine and EtOAc (2×200 ml). The combined organic layers were washed with brine, dried with sodium sulfate (dried), and evaporated (evap.). Purification by chromatography on silica (silica gel (240-400 mesh) from EM Science) using 20 to 40% EtOAc/DCM gave 11.1 g of 5'-Azido-N6-benzoyl-3'-O-t-butyldimethylsilyl-2',5'-dideoxyadenosine as a white foam: NMR (300 MHz,d6-DMSO) δ11.25 (br, 1H), 8.78 (s,1H), 8.71 (s, 1H), 8.05 (m, 2H), 7.5-7.7 (m, 3H), 6.52 (t, 1H,J=7 Hz), 4.72 (m, 1H), 4.02 (m,1H), 3.67 (dd,1H, J=13,7 Hz), 3.56 (dd,1H,J=13,5 Hz), 3.09 (m, 1H), 2.43 (m,1H), 0.92 (s,9H), 0.14 (s,6H).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was partitioned between one half saturated brine and EtOAc (2×200 ml)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with sodium sulfate (dried)
  5. customevaporated (evap.)
  6. customPurification by chromatography on silica (silica gel (240-400 mesh) from EM Science)

Sources & evidence

ORD record
ord-7ea091a4095d4bbb8540a2f88200082d
Source dataset
uspto-grants-1995_11
Patent number
US05470967

Reaction notes

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