Trifluoroacetic acid → 2-(4-Fluoro-3,5-dimethyl-phenylamino)-hexanoic acid hydroxyamide

HRID 885503노트

반응식

HRID 885503 반응식
C([O:5][NH:6][C:7](=[O:23])[C@H:8]([NH:13][C:14]1[CH:19]=[C:18]([CH3:20])[C:17]([F:21])=[C:16]([CH3:22])[CH:15]=1)[CH2:9][CH2:10][CH2:11][CH3:12])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[OH:5][NH:6][C:7](=[O:23])[CH:8]([NH:13][C:14]1[CH:19]=[C:18]([CH3:20])[C:17]([F:21])=[C:16]([CH3:22])[CH:15]=1)[CH2:9][CH2:10][CH2:11][CH3:12]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86667068(R)-2-(4-Fluoro-3,5-dimethyl-phenylamino)-hexanoic acid tert-butoxy-amide

생성물 1

HCID 866670692-(4-Fluoro-3,5-dimethyl-phenylamino)-hexanoic acid hydroxyamide수율 30%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (R)-2-(4-fluoro-3,5-dimethyl-phenylamino)-hexanoic acid tert-butoxy-amide (0.737 g, 2.273 mmol) in 1 mL of dichloromethane, was added trifluoroacetic acid (9 mL). After stirring at room temperature for 87 h, the reaction mixture was concentrated under reduced pressure. The product was isolated by Flash chromatography (silica gel) eluting with 0-10% methanol/dichoromethane to give the title compound as a white solid (0.182 g, 30% yield). Pure analytical sample was obtained by RP-HPLC purification. LC-MS: tR=6.8 min; m/z 269 (M+H)+;)+; 1H NMR (500 MHz, CD3OD) δ 0.92 (t, J=7.05 Hz, 3H), 1.33-1.45 (m, 4H), 1.71-1.79 (m, 2H), 2.13 (d, J=2.02 Hz, 6H), 3.65 (t, J=7.05 Hz, 1H), 6.36 (d, J=5.88 Hz, 2H); 13C NMR (125.75 MHz, CD3OD) δ 14.24, 14.80, 23.50, 29.18, 33.99, 58.94, 115.65 (d, J=3.14 Hz), 125.69 (d, J=18.74 Hz), 143.30, 155.19 (d, J=233.14 Hz), 172.75; 19F NMR (470.58 MHz, CD3OD) δ −135.79.

후처리

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe product was isolated by Flash chromatography (silica gel)
  3. washeluting with 0-10% methanol/dichoromethane

출처 및 근거

ORD 기록
ord-88e79117351645df95382155768dfdb5
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242174B2

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