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Sodium Iodide → Methyl (S)-2-(Boc-amino)-4-iodobutanoate

HRID 909214
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인쇄 미리보기

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HRID 909214 반응식
[CH3:1][O:2][C:3](=[O:16])[C@@H:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:6]Br.[Na+].[I-:18]>CC(C)=O>[CH3:1][O:2][C:3](=[O:16])[C@@H:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:6][I:18]
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참가 물질

4

반응물 2

HCID 5238Sodium IodideHCID 10685328Methyl (S)-2-(Boc-amino)-4-bromobutyrate

생성물 1

HCID 14394150Methyl (S)-2-(Boc-amino)-4-iodobutanoate수율 92%

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
70 °C

실험 절차

A mixture of (S)-4-bromo-2-tert-butoxycarbonylaminobutyric acid methyl ester (1.19 g, 4.0 mmol) (Example 120, Steps A-D) and NaI (6.0 g, 40.0 mmol) in acetone (25 mL) was heated to 70° C. for 2 hours. The mixture was then cooled to room temperature, concentrated under reduced pressure and partitioned between water (10 mL) and ether (40 mL). The layers were separated and the organic layer was washed with water (10 mL), dried over MgSO4, filtered through Celite, and concentrated under reduced pressure to afford 1.26 g of the product (92% yield).

후처리

  1. temperatureThe mixture was then cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. custompartitioned between water (10 mL) and ether (40 mL)
  4. customThe layers were separated
  5. washthe organic layer was washed with water (10 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered through Celite
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-be72583203b841179e40dc5c13241b5e
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08017641B2

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