Trimethylamine oxide → HCID 25051365, compound

HRID 1020255Notes

Reaction equation

HRID 1020255 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][O:16][CH2:17]C=C)[N:14]=1)=[O:8].C[N+]([O-])(C)C.[C:29]([O-:32])(O)=O.[Na+].C[C:35](C)=[O:36].O>O=[Os](=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][O:16][CH2:17][CH:29]([OH:32])[CH2:35][OH:36])[N:14]=1)=[O:8]

Participants

6

Reactant 4

HCID 1145Trimethylamine oxideHCID 516892Sodium BicarbonateHCID 18366337Propan-2-one--water (1/1)HCID 25051364HCID 25051364, compound

Product 1

HCID 25051365HCID 25051365, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a solution of 1-(3,4-dichlorobenzyl)-3-(4-(allyloxymethyl)thiazol-2-yl)urea (Example 90, 100 mg, 0.27 mmol) in a mixture of acetone/water 10/1 (2 ml) was added TMANO (trimethylamine N-oxide, 45 mg, 0.40 mmol) and a OsO4 solution (4% in water, 0.34 mL, 5.4 μmol). The mixture was stirred at room temperature for 3 h and a saturated NaHCO3 solution was added. The solution was extracted with EtOAc (2×25 mL) and the combined extracts were dried over Na2SO4, filtered, and concentrated in vacuo to afford 100 mg of an off-white solid. Purification by column chromatography (SiO2, DCM/4% 7N NH3 in MeOH). 1H-NMR (300 MHz, CDCl3): δ 7.34 (s, 1H), 7.33 (d, 1H), 7.08 (d, 1H), 7.05 (bs, 1H), 6.62 (s, 1H), 4.38 (s, 2H). 4.33 (d, 2H), 3.86 (t, 1H), 3.62-3.50 (m, 4H).

Workup

  1. extractionThe solution was extracted with EtOAc (2×25 mL)
  2. dry with materialthe combined extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d912d04c4f8f48e1af70eeb9bd282146
Source dataset
uspto-grants-2014_05
Patent number
US08716320B2

Reaction notes

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