Pyridine → (R)-1-fluoro-1-oxo-3-phenylpropan-2-yl acetate

HRID 1628219Notes

Reaction equation

HRID 1628219 reaction equation
[C:1]([O:4][C@H:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6](O)=[O:7])(=[O:3])[CH3:2].N1C=CC=CC=1.N1C(F)=NC(F)=NC=1[F:24]>C(Cl)Cl>[C:1]([O:4][C@H:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6]([F:24])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 11469837(R)-2-acetoxy-3-phenylpropanoic acid

Product 1

HCID 87562668(R)-1-fluoro-1-oxo-3-phenylpropan-2-yl acetateYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(R)-2-acetoxy-3-phenylpropanoic acid 11.1.C (1170 mg, 5619 μmol) was azeotroped and dissolved in DCM under nitrogen. Pyridine (454 μl, 5619 μmol) was added followed by cyanuric fluoride (1423 μl, 16858 μmol) at −20° C. After 1 h, reaction was worked up with ice and DCM to afford 1.04 g (88%) crude (R)-1-fluoro-1-oxo-3-phenylpropan-2-yl acetate 11.1.D. The crude was directly used for next step.

Workup

  1. customreaction

Sources & evidence

ORD record
ord-7942f49565a447b6b5331efd5cd4e146
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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