Ethyl Acetate → HCID 18512114, compound

HRID 1370804Notes

Reaction equation

HRID 1370804 reaction equation
C(O[C:5]1[CH:31]=[CH:30][C:8]([CH2:9][N:10]([CH2:23][C:24]2[CH:29]=CC=[CH:26][CH:25]=2)[C:11]2[C:12]([CH3:22])=[C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)C=C.C[N+]1([O-])CC[O:36][CH2:35]C1.[OH:40]S([O-])=O.[Na+].[C:45]([O:48][CH2:49][CH3:50])(=O)[CH3:46]>CC(C)=O.O.[Os](=O)(=O)(=O)=O.N12CCN(CC1)CC2>[CH2:9]([N:10]([CH2:23][C:24]1[CH:25]=[CH:26][C:45]([O:48][CH2:49][CH:50]([OH:40])[CH2:35][OH:36])=[CH:46][CH:29]=1)[C:11]1[C:12]([CH3:22])=[C:13]([NH:17][S:18]([CH3:21])(=[O:19])=[O:20])[CH:14]=[CH:15][CH:16]=1)[C:8]1[CH:7]=[CH:6][CH:5]=[CH:31][CH:30]=1

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxide2×HCID 18512192HCID 18512192, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 18512114HCID 18512114, compoundYield 95%

Reagents, catalysts & solvents 4

HCID 9237DabcoCatalystHCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

The product from Example 19B (2.93 g, 6.72 mmoles ) and 4-methyl-morpholine N-oxide (0.8660 g, 7.4 mmoles) in acetone (30 mL) and water (4.3 mL) were treated with osmium tetroxide (1.7 mL, 0.0168 mmoles, 2.5 wt % solution in 2-methyl-2-propanol) and allowed to stirr at room temperature overnight. The mixture was then treated with 1,4-Diazabicyclo[2.2.2]octane (0.05 g) and 4-methyl-morpholine N-oxide (0.8660 g, 7.4 mmoles) and allowed to stir for an additional 24 hours. Saturated NaHSO3 (250 mL) and ethyl acetate (250 mL) were added and the reaction mixture was stirred vigorously for 2.5 hours. The mixture was partitioned and the organic phase washed with brine, dried (Na2SO4), filtered and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, ethyl acetate) to provide the title compound as a yellow oil (3.0 g, 95%).

Workup

  1. stirringthe reaction mixture was stirred vigorously for 2.5 hours
  2. customThe mixture was partitioned
  3. washthe organic phase washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-42c70ba4796546d7a88408bd9dba786d
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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