Carbon tetrabromide → Methyl (S)-2-(Boc-amino)-4-bromobutyrate

HRID 909197노트

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HRID 909197 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]O.C(Br)(Br)(Br)[Br:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[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:18]

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 10561607Methyl N-(tert-butoxycarbonyl)-L-homoserinate

생성물 1

HCID 10685328Methyl (S)-2-(Boc-amino)-4-bromobutyrate수율 76%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a cooled (0° C.) solution of (S)-2-tert-butoxycarbonylamino-4-hydroxy-butyric acid methyl ester (28.7 g, 123 mmol) in dichloromethane (500 mL) was added CBr4 (51.0 g, 154 mmol). The mixture was stirred for 5 minutes before the portion-wise addition of triphenylphosphine (48.41 g, 185 mmol). The mixture continued to stir at 0° C. for 1 hour and was then allowed to warm to room temperature. The solvent was removed under reduced pressure and was then diluted with ether (500 mL) and stirred for 30 minutes. The mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was chromatographed eluting with ether/hexanes (1:2) to afford 27.5 g of white solid (76% yield).

후처리

  1. temperatureto warm to room temperature
  2. customThe solvent was removed under reduced pressure
  3. additionwas then diluted with ether (500 mL)
  4. stirringstirred for 30 minutes
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was chromatographed
  8. washeluting with ether/hexanes (1:2)

출처 및 근거

ORD 기록
ord-872e654fd7284595a6d3dab6cca97e21
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017641B2

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