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Diisopropylethylamine → Tert-butyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-oxoethyl)-3-(2-hydroxyethyl)piperazine-1-carboxylate

HRID 1502082
ノート
印刷プレビュー

反応式

HRID 1502082 の反応式
Br[CH2:2][C:3]([C:5]1[C:6]([CH3:14])=[C:7]([C:10]([F:13])=[CH:11][CH:12]=1)[C:8]#[N:9])=[O:4].[OH:15][CH2:16][CH2:17][CH:18]1[NH:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]1.CCN(C(C)C)C(C)C>C1COCC1.[Cl-].[Na+].O>[C:8]([C:7]1[C:6]([CH3:14])=[C:5]([C:3](=[O:4])[CH2:2][N:23]2[CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:19][CH:18]2[CH2:17][CH2:16][OH:15])[CH:12]=[CH:11][C:10]=1[F:13])#[N:9]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 53407692tert-Butyl 3-(2-hydroxyethyl)piperazine-1-carboxylateHCID 867270493-(2-Bromo-acetyl)-6-fluoro-2-methyl-benzonitrile

生成物 1

HCID 89619114Tert-butyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-oxoethyl)-3-(2-hydroxyethyl)piperazine-1-carboxylate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒
HCID 57417360
Sodium chloride; water
溶媒

実験手順

3-(2-Bromoacetyl)-6-fluoro-2-methylbenzonitrile (prepared as described above, 5.11 g, 20.0 mmol) was dissolved in THF (100 mL), then known, commercially available compound tert-butyl 3-(2-hydroxyethyl)piperazine-1-carboxylate (4.60 g, 20.0 mmol) was added, followed by Hunig's base (6.96 mL, 39.9 mmol) and the mixture was stirred overnight. The reaction mixed was poured into brine and extracted with ethyl acetate (twice), dried over Na2SO4, filtered and concentrated. The product was purified by MPLC chromatography using a 330 g ISCO Redi Sep column and 5% MeOH/DCM solvent system-to yield tert-butyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-oxoethyl)-3-(2-hydroxyethyl)piperazine-1-carboxylate: LC-MS (IE, m/z): 406 [M+1]+;

後処理

  1. additionThe reaction mixed
  2. extractionextracted with ethyl acetate (twice),
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by MPLC chromatography

出典と根拠

ORDレコード
ord-595fc8d3918c4789823db85ea7012c2d
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09206199B2

反応ノート

読み込み中…

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