Hydrochloric Acid → HCID 72215606, compound

HRID 1426321Notes

Reaction equation

HRID 1426321 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[N:8]=[C:7]([C:9]([OH:11])=[O:10])[CH:6]=[C:5]([CH:12]=C)[CH:4]=1.I([O-])(=O)(=O)=[O:17].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+].Cl>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH:12]([C:5]1[CH:4]=[C:3]([C:2]([F:15])([F:14])[F:1])[N:8]=[C:7]([C:9]([OH:11])=[O:10])[CH:6]=1)=[O:17]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24477Sodium ThiosulfateHCID 23667635Sodium periodateHCID 69673041HCID 69673041, compound2×

Product 1

HCID 72215606HCID 72215606, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

6-(Trifluoromethyl)-4-vinylpyridine-2-carboxylic acid (0.30 g, 0.69 mmol, the crude product from Step A) was dissolved in 1,4-dioxane (20. mL) and water (5.0 mL), then sodium periodate (0.44 g, 2.1 mmol, Aldrich) was added, followed by 4 wt % osmium tetraoxide in water (0.152 mL, 0.0240 mmol, Aldrich). The reaction was stirred overnight. Sodium thiosulfate solution was added and the mixture was stirred for 30 minutes. 1N HCl was added to adjust the pH to between 4 and 5, and the product was extracted with ten portions of 10% isopropanol in CHCl3. The combined extracts were dried over sodium sulfate, filtered and concentrated. Flash chromatography on silica gel, eluting with a gradient from 0-10% MeOH in DCM afforded a partially purified product (94 mg, 20% yield over Steps A & B). 1H NMR (300 MHz, CDCl3) δ 10.25 (s, 1H), 8.83 (d, J=0.8 Hz, 1H), 8.38 (d, J=1.3 Hz, 1H).

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. extractionthe product was extracted with ten portions of 10% isopropanol in CHCl3
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washFlash chromatography on silica gel, eluting with a gradient from 0-10% MeOH in DCM
  7. customafforded a partially purified product (94 mg, 20% yield over Steps A & B)

Sources & evidence

ORD record
ord-b4f15f70563c4649a40b0eb8146b0688
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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