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Methyl iodide → (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-methoxy-3-methylbutanoic acid

HRID 1471052
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HRID 1471052 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([OH:16])([CH3:15])[CH3:14])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:20]>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([O:16][CH3:20])([CH3:15])[CH3:14])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11075314(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-hydroxy-3-methylbutanoic acid

생성물 1

HCID 59611493(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-methoxy-3-methylbutanoic acid수율 43%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of Example 203A (363 mg, 1.56 mmol) in THF (7 mL) at 0° C. was added NaH (373 mg, 9.34 mmol) and stirring was continued for 15 min. Iodomethane (0.78 mL, 12.45 mmol) was added and the solution was allowed to warm to room temperature and stirred for 18 h. Solution was quenched with H2O, diluted with EtOAc, washed with H2O, brine, dried (Na2SO4), filtered and solvent removed to give the title compound (165 mg, 0.67 mmol, 43%). MS (ESI) m/z 248 (M+H)+.

후처리

  1. stirringstirred for 18 h
  2. customSolution was quenched with H2O
  3. additiondiluted with EtOAc
  4. washwashed with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customsolvent removed

출처 및 근거

ORD 기록
ord-1b1946b820d746b78f7ee16efcda94c9
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09006387B2

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