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

HRID 885503ノート

反応式

HRID 885503 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-88e79117351645df95382155768dfdb5
出典データセット
uspto-grants-2012_08
特許番号
US08242174B2

反応ノート

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