Ethanol → 5-Fluoro-2-(2-isobutyl-3-methyl-benzoylamino)-indan-2-carboxylic acid

HRID 1047795노트

반응식

HRID 1047795 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]([NH:14][C:15](=[O:26])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:17]=1/[CH:23]=[CH:24]/[CH3:25])([C:11]([OH:13])=[O:12])[CH2:5]2.[CH3:27]CO>[Pd]>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]([NH:14][C:15](=[O:26])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:17]=1[CH2:23][CH:24]([CH3:27])[CH3:25])([C:11]([OH:13])=[O:12])[CH2:5]2

참가 물질

4

반응물 2

HCID 702EthanolHCID 251608005-Fluoro-2-[3-methyl-2-((E)-propenyl)-benzoylamino]-indan-2-carboxylic acid

생성물 1

HCID 251606695-Fluoro-2-(2-isobutyl-3-methyl-benzoylamino)-indan-2-carboxylic acid수율 78%

시약·촉매·용매 1

HCID 23938Palladium촉매

실험 절차

5-Fluoro-2-[3-methyl-2-((E)-propenyl)-benzoylamino]-indan-2-carboxylic acid (154) (270 mg, 0.76 mmol) is dissolved in absolute EtOH (15 mL) by heating. The resulting solution is cooled down to RT under argon and then is added the catalyst, Pd—C (5 wt. % Pd, 125 mg, 5.9% mmol). The resulting reaction mixture is moved to the Paar apparatus to run hydrogenation: 50 psi, 50° C., overnight. The catalyst is removed by filtration through a pre-column (10 g silica gel) and washed with EtOH. The combined organic solution is concentrated in vacuo. The residue is purified by HPLC to give a pure product (155) as white solid (210 mg, 78%).

후처리

  1. temperatureby heating
  2. customThe resulting reaction mixture
  3. custom50 psi, 50° C., overnight
  4. customThe catalyst is removed by filtration through a pre-column (10 g silica gel)
  5. washwashed with EtOH
  6. concentrationThe combined organic solution is concentrated in vacuo
  7. customThe residue is purified by HPLC

출처 및 근거

ORD 기록
ord-81549fef3bc04928a16d129eaefd0dfb
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569535B2

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