Pyridine → HCID 117599491, compound

HRID 716111Notes

Reaction equation

HRID 716111 reaction equation
[F:1][C@:2]1([CH2:17][OH:18])[O:6][C@@H:5]([N:7]2[CH:14]=[CH:13][C:11](=[O:12])[NH:10][C:8]2=[O:9])[C@H:4]([OH:15])[C@@H:3]1[OH:16].[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCOC(C)=O.N1C=C[CH:37]=[CH:36][CH:35]=1>>[C:19]([O:18][CH2:17][C@:2]1([F:1])[C@@H:3]2[C@@H:4]([O:15][C:36]([CH3:37])([CH3:35])[O:16]2)[C@H:5]([N:7]2[CH:14]=[CH:13][C:11](=[O:12])[NH:10][C:8]2=[O:9])[O:6]1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8857Ethyl AcetateHCID 54260440HCID 54260440, compound

Product 1

HCID 117599491HCID 117599491, compoundYield 83%

Procedure

The protected 4′-fluorouridine (A1, 3.0 g, 9.93 mmol, 1 eq.) was dissolved in anhydrous pyridine (15 mL). The mixture was stirred under an argon atmosphere while benzoyl chloride (1.73 mL, 2.05 g, 14.3 mmol, 1.5 eq) was added drop-wise at room temperature. The mixture was stirred at room temperature and was followed by tlc (silica gel, 100% EtOAc). The reaction was complete within 30 minutes. The reaction mixture was concentrated under reduced pressure and purified by CombiFlash® column chromatography (Silica gel; 0 to 100% EtOAc:Heptane). The benzyloxy protected product (A2, 3.35 g, 83%) was obtained as a white-colored solid.

Workup

  1. additionwas added drop-wise at room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by CombiFlash® column chromatography (Silica gel; 0 to 100% EtOAc:Heptane)

Sources & evidence

ORD record
ord-2d5d5fa09e654d3ca4584121b2bf4d84
Source dataset
uspto-grants-2015_11
Patent number
US09187515B2

Reaction notes

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