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

HRID 2040015ノート

反応式

HRID 2040015 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4072e8ef09ef406db3b81e140b74cd9b
出典データセット
uspto-grants-2013_11
特許番号
US08580777B2

反応ノート

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