Methyl morpholine oxide → 4-Formyl-2-phenylbenzoyl methionine methyl ester

HRID 325217

Reaction equation

HRID 325217 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C@H:4]([CH2:21][CH2:22][S:23][CH3:24])[NH:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][C:8]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C[C:27]1(C)CC(C)OB(C=C)[O:28]1.C[N+]1([O-])CCOCC1>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].O.O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3](=[O:25])[C@H:4]([CH2:21][CH2:22][S:23][CH3:24])[NH:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][C:10]([CH:27]=[O:28])=[CH:9][C:8]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

10

Reactant 3

HCID 82029Methyl morpholine oxideHCID 1073104,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinaneHCID 20622824(2-Phenyl4bromobenzoyl)-methionine methyl ester

Product 1

HCID 105712674-Formyl-2-phenylbenzoyl methionine methyl ester

Reagents, catalysts & solvents 6

HCID 30318Osmium TetroxideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 10340Sodium CarbonateSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
25 °C

Procedure

A mixture of (2-phenyl-4-bromobenzoyl) methionine methyl ester (100 mmol), 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane (100 mmol), tetrakis(triphenylphosphine)palladium (0) (3 mmol) in toluene and 2 M sodium carbonate in water (100 mL) is heated at 80° C. until the starting methyl ester disappears. The resulting mixture is extracted with ether, and washed with water, brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue is then purified by column chromatography on silica gel. To a solution of the resulting vinyl compound in dioxane/water (4/1) is added osmium tetraoxide (0.03 equivalent), N-methylmorpholine N-oxide (3 equivalents), and the reaction is stirred at 25° C. until TLC analysis shows the reaction to be complete. The reaction mixture is extracted with ether, which is washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue is then purified by column chromatography on silica gel to afford the title product.

Workup

  1. extractionThe resulting mixture is extracted with ether
  2. washwashed with water, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is then purified by column chromatography on silica gel
  7. customthe reaction
  8. extractionThe reaction mixture is extracted with ether, which
  9. washis washed with water and brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe residue is then purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-be157c7f9f90487b94fc7114f8218bd8
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Linked notes

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