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

HRID 325217

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HRID 325217 반응식
[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

참가 물질

10

반응물 3

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

생성물 1

HCID 105712674-Formyl-2-phenylbenzoyl methionine methyl ester

시약·촉매·용매 6

HCID 30318Osmium Tetroxide촉매HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 1140Toluene용매HCID 10340Sodium Carbonate용매HCID 218864351,4-Dioxane--water (1/1)용매

반응 조건

온도
25 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-be157c7f9f90487b94fc7114f8218bd8
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06221865B1

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