L-Serine → 2-acetamido-3-(6-chloro-5-fluoro-1H-indol-3-yl)propanoic acid

HRID 1946557ノート

反応式

HRID 1946557 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[F:11].[CH3:12][C:13](OC(C)=O)=[O:14].[NH2:19][C@H:20]([C:23]([OH:25])=[O:24])[CH2:21]O>CC(O)=O>[C:13]([NH:19][CH:20]([CH2:21][C:6]1[C:5]2[C:9](=[CH:10][C:2]([Cl:1])=[C:3]([F:11])[CH:4]=2)[NH:8][CH:7]=1)[C:23]([OH:25])=[O:24])(=[O:14])[CH3:12]

参加物

5

反応物 3

HCID 5951L-SerineHCID 7918Acetic AnhydrideHCID 27736486-Chloro-5-fluoro-1H-indole

生成物 1

HCID 579487332-acetamido-3-(6-chloro-5-fluoro-1H-indol-3-yl)propanoic acid収率 37%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
80 °C

実験手順

To a solution of 6-chloro-5-fluoroindole (1.8 g, 10.8 mmol) and Ac2O (10 mL) in AcOH (30 mL) was added L-serine (2.2 g, 20.9 mmol), the mixture was heated to 80° C. After TLC indicated the reaction was complete, the mixture was cooled to 0° C.; neutralized to pH 11, and washed with MTBE. The aqueous phase was acidified to pH 2 and extracted with EtOAc. The combined organic layers were washed with water and brine, dried with Na2SO4, filtered, and concentrated. The residue was purified with chromatography (Petroleum ether/EtOAc 1:1) to give 2-acetylamino-3-(6-chloro-5-fluoro-1H-indol-3-yl)-proprionic acid as a light yellow solid (1.2 g, 37% yield).

後処理

  1. temperaturethe mixture was cooled to 0° C.
  2. washwashed with MTBE
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified with chromatography (Petroleum ether/EtOAc 1:1)

出典と根拠

ORDレコード
ord-c84b30f45cc84e52a10b3171dae5dfa6
出典データセット
uspto-grants-2013_03
特許番号
US08399453B2

反応ノート

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