Ethyl Acetate → HCID 117599995, compound

HRID 716112Notes

Reaction equation

HRID 716112 reaction equation
[C:1]([O:9][CH2:10][C@:11]1([F:29])[C@@H:18]2[C@@H:14]([O:15]C(C)(C)[O:17]2)[C@H:13]([N:21]2[CH:26]=[CH:25][C:24](=[O:27])[NH:23][C:22]2=[O:28])[O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCOC(C)=O>C(O)=O.O>[C:1]([O:9][CH2:10][C@:11]1([F:29])[C@@H:18]([OH:17])[C@@H:14]([OH:15])[C@H:13]([N:21]2[CH:26]=[CH:25][C:24](=[O:27])[NH:23][C:22]2=[O:28])[O:12]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 117599491HCID 117599491, compound

Product 1

HCID 117599995HCID 117599995, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

The benzyloxy protected fluoro nucleoside (A2, 3.0 g, 8.25 mmol) was dissolved in formic acid (95%, 30 mL) to which water (3 mL) was added. The mixture was stirred at room temperature and was followed by tlc (silica gel, 100% EtOAc). The reaction was shown to be complete in 3 hours. The reaction mixture was concentrated by rotary evaporation keeping the bath temperature <30° C. The crude product was purified by CombiFlash® column chromatography (Silica gel; 0 to 100% EtOAc:Heptane) providing the desired material in 83% yield (3, 2.8 g).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated by rotary evaporation
  3. customthe bath temperature <30° C
  4. customThe crude product was purified by CombiFlash® column chromatography (Silica gel; 0 to 100% EtOAc:Heptane)

Sources & evidence

ORD record
ord-a48b7a4baad94619a1ee5d82ec26b15d
Source dataset
uspto-grants-2015_11
Patent number
US09187515B2

Reaction notes

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