Acetone → N-(2-Acetyl-phenyl)-2,3-dihydroxy-3-methyl-butyramide

HRID 584777Notes

Reaction equation

HRID 584777 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=CC=1NC(=O)C=C(C)C)(=[O:3])[CH3:2].C[N+:18]1([O-])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.CC[O:27]C(C)=O.[CH3:31][C:32]([CH3:34])=[O:33]>O.O=[Os](=O)(=O)=O>[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:22][C:23]=1[NH:18][C:19](=[O:27])[CH:20]([OH:21])[C:32]([OH:33])([CH3:34])[CH3:31])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 180AcetoneHCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxideHCID 208216943-Methyl-but-2-enoic acid (2-acetyl-phenyl)-amide

Product 1

HCID 22341823N-(2-Acetyl-phenyl)-2,3-dihydroxy-3-methyl-butyramideYield 99%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

To the product of Example 10 (440 mg, 2.03 mmol) in acetone (4 mL) and H2O (1 mL) was added 4-methylmorpholine N-oxide (269 mg, 2.23 mmol), and 2.5 wt % OsO4 (0.25 mL, 0.02 mmol). The reaction mixture was stirred at room temperature for 26 h. EtOAc was added to the reaction mixture, and the resulting solution was washed with aqueous sodium bisulfite, brine and dried over MgSO4. After evaporation of the volatiles, the crude product (505 mg, 99% yield) was clean enough to carry on the next step. 1H NMR (360 MHz, CDCl3) δ 8.69-8.61 (m, 1H), 7.85-7.77 (m, 1H), 7.75-7.42 (m, 1H), 7.12-7.04 (m, 1H), 4.88 (d, J=5.4 Hz, 1H), 4.10 (s, 1H), 4.07 (d, J=5.4 Hz, 1H), 2.57 (s, 3H), 1.27 (s, 3H), 1.25 (s, 3H).

Workup

  1. washthe resulting solution was washed with aqueous sodium bisulfite, brine
  2. dry with materialdried over MgSO4
  3. customAfter evaporation of the volatiles

Sources & evidence

ORD record
ord-7e1a8dac6f9a4e6190e6c38c6de75e2c
Source dataset
uspto-grants-2005_08
Patent number
US06927294B1

Reaction notes

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