Peracetic Acid → HCID 58042458, compound

HRID 2048048Notes

Reaction equation

HRID 2048048 reaction equation
C(OO)(=[O:3])C.[Cl:6][C:7]1[C:8]([O:22][CH:23]2[CH2:26][CH2:25][CH2:24]2)=[N:9][CH:10]=[C:11](B2OC(C)(C)C(C)(C)O2)[CH:12]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)(=O)C.O>[Cl:6][C:7]1[CH:12]=[C:11]([OH:3])[CH:10]=[N:9][C:8]=1[O:22][CH:23]1[CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 3

HCID 6585Peracetic AcidHCID 24477Sodium ThiosulfateHCID 58042444HCID 58042444, compound

Product 1

HCID 58042458HCID 58042458, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Acetic acid solution of peracetic acid (35%, 4.2 mL, 21.3 mmol) was added to a solution of 3-chloro-2-cyclobutoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (Preparation 20, 4.4 g, 14.2 mmol) in glacial acetic acid (26 mL) and water (13 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour. Aqueous solution of sodium thiosulfate (0.5 M, 80 mL) was added and the mixture was stirred for 30 minutes at room temperature. The aqueous layer was extracted with EtOAc (3×40 mL). The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography eluting with 10% EtOAc in heptane to afford the title compound as a clear oil (2.05 g, 72%):

Workup

  1. stirringthe mixture was stirred for 30 minutes at room temperature
  2. extractionThe aqueous layer was extracted with EtOAc (3×40 mL)
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by silica gel chromatography
  7. washeluting with 10% EtOAc in heptane

Sources & evidence

ORD record
ord-d5d54b034262444898681d256eed82f6
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

Loading…