Benzoyl chloride → HCID 117793648, compound

HRID 515937Notes

Reaction equation

HRID 515937 reaction equation
[F:1][C@:2]1([CH3:17])[C@H:6]([OH:7])[C:5](=[CH2:8])[O:4][C@H:3]1[N:9]1[CH:14]=[CH:13][C:12](=[O:15])[NH:11][C:10]1=[O:16].[C:18](Cl)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19].C([O-])(O)=O.[Na+]>CN(C1C=CN=CC=1)C.C1COCC1>[O:16]=[C:10]1[NH:11][C:12](=[O:15])[CH:13]=[CH:14][N:9]1[C@@H:3]1[O:4][C:5](=[CH2:8])[C@@H:6]([O:7][C:18](=[O:19])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@:2]1([F:1])[CH3:17]

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 66802966HCID 66802966, compound

Product 1

HCID 117793648HCID 117793648, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of chiral 1-((2R,3R,4R)-3-fluoro-4-hydroxy-3-methyl-5-methylene-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (18.3 g, 75.6 mmol) and DMAP (27.7 g, 227 mmol) in anhydrous THF (900 mL) at 0° C. was added BzCl (15.9 g, 113.4 mmol) dropwise. The reaction mixture was stirred at 0° C. for 0.5 h, then sat. NaHCO3 was added to quench the reaction. The mixture was extracted with EA (300 mL×3). The combined organic extract was washed with H2O, brine, dried over Na2SO4, and concentrated. The residue was purified by silica gel chromatography column (DCM:MeOH=160:1 to 120:1) to give the title compound as a white solid (17 g, 65%).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with EA (300 mL×3)
  4. extractionThe combined organic extract
  5. washwas washed with H2O, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography column (DCM:MeOH=160:1 to 120:1)

Sources & evidence

ORD record
ord-dc591d6612d4474886ed8df26a918543
Source dataset
uspto-grants-2015_08
Patent number
US09108999B2

Reaction notes

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