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

HRID 1946557노트

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HRID 1946557 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c84b30f45cc84e52a10b3171dae5dfa6
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399453B2

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