Allyl bromide → (R)-3-(4-Allyloxy-3-fluorophenyl)-2-tert-butoxycarbonylaminopropionic acid

HRID 2040015노트

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HRID 2040015 반응식
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C@H:11]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([F:23])[CH:17]=1)[C:12]([OH:14])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH2:24](Br)[CH:25]=[CH2:26]>CN(C=O)C>[CH2:26]([O:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][C@@H:11]([NH:10][C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:9])[C:12]([OH:14])=[O:13])=[CH:17][C:18]=1[F:23])[CH:25]=[CH2:24]

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 40429673N-Boc-3-fluoro-D-tyrosine

생성물 1

HCID 67028604(R)-3-(4-Allyloxy-3-fluorophenyl)-2-tert-butoxycarbonylaminopropionic acid수율 99.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

1.18 g (60%, 29.39 mmol) of sodium hydride were added to a solution of 4.0 g (13.36 mmol) of (R)-2-tert-butoxycarbonylamino-3-(3-fluoro-4-hydroxyphenyl)propionic acid in 23 ml of DMF while stirring at 0° C., and the mixture was stirred at this temperature. After 15 min, 1.27 ml (1.78 g, 14.7 mmol) of allyl bromide were added, and stirring was continued for 1 h while the mixture reached RT. It was quenched with methanol and, after cooling, excess methanol was removed in a rotary evaporator. Dilution with diethyl ether was followed by acidification with 1N hydrochloric acid, and the aqueous phase was extracted twice more with diethyl ether, and the combined organic phases were washed with saturated sodium chloride solution, dried over NaSO4, filtered and concentrated. 4.50 g of a yellowish oil were obtained.

후처리

  1. stirringthe mixture was stirred at this temperature
  2. stirringstirring
  3. waitwas continued for 1 h while the mixture
  4. customreached RT
  5. customIt was quenched with methanol
  6. temperatureafter cooling
  7. customexcess methanol was removed in a rotary evaporator
  8. extractionthe aqueous phase was extracted twice more with diethyl ether
  9. washthe combined organic phases were washed with saturated sodium chloride solution
  10. dry with materialdried over NaSO4
  11. filtrationfiltered
  12. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4072e8ef09ef406db3b81e140b74cd9b
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580777B2

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