Ethyl Acetate → HCID 11049546, compound

HRID 2301682Notes

Reaction equation

HRID 2301682 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:24][C@H:23]([CH2:25][O:26][C:27]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:22][C@H:12]1OC1N=CC(=S(=O)=O)N=1.[FH:46].F.F.C(N(CC)CC)C.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:24][C@H:23]([CH2:25][O:26][C:27]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:22][C@@H:12]1[F:46]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 516892Sodium BicarbonateHCID 18345597HCID 18345597, compound

Product 1

HCID 11049546HCID 11049546, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

113 mg (0.176 mmols) of 6-chloro-9-[2-O-(sulfurylimidazolyl)-3-deoxy-5-O-(triphenylmethyl)-β-D-erythro-pentofuranosyl]-9H-purine was dissolved in 1.80 ml of toluene, to which was added 0.18 ml (1.06 mmols) of triethylamine trihydrofluoride, and stirred overnight at 50° C. After having been cooled, 10.0 ml of ethyl acetate and 8.0 ml of an aqueous saturated solution of sodium hydrogencarbonate were added to this, to separate it into layers. The organic layer was dried with anhydrous sodium sulfate, and filtered. Then, the solvent was evaporated from the filtrate. The residue was dissolved in acetonitrile and analyzed through liquid chromatography. The intended product was obtained at an yield of 41.9%.

Workup

  1. temperatureAfter having been cooled
  2. customto separate it into layers
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThen, the solvent was evaporated from the filtrate
  6. dissolutionThe residue was dissolved in acetonitrile
  7. customThe intended product was obtained at an yield of 41.9%

Sources & evidence

ORD record
ord-76acda0900014925a5d01b6454a09bbf
Source dataset
uspto-grants-2002_12
Patent number
US06500946B1

Reaction notes

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