4-(4-Hydroxyphenyl)butanoic acid → 4-(4-hydroxyphenyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

HRID 885710ノート

反応式

HRID 885710 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:4][CH:3]=1.[O:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[O:20][NH2:21]>ClCCl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][C:11]([NH:21][O:20][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][O:14]2)=[O:13])=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 2799834-(4-Hydroxyphenyl)butanoic acidHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamine

生成物 1

HCID 866595084-(4-hydroxyphenyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide収率 65%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 4-(4-Hydroxyphenyl)butanoic acid (0.90 g, 5 mmol), O-(tetrahydro-2H-pyran-2-yl)hydroxylamine (0.59 g, 5 mmol) and 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (1.15 g, 6 mmol) in 50 mL dichloromethane was stirred at room temperature for 2 h (monitored by TLC). The mixture was extracted with water and dried over magnesium sulfate. The residue was purified by chromatography (MeOH:DCM=1:50) to give the title compound (0.84 g, 65%). NMR (400 MHz in DMSO, Bruker AVANCE-400): δ 1.50 (m, 3H, OTHP), 1.71 (m, 3H, OTHP), 1.73 (m, 2H, CH2), 1.96 (m, 2H, CH2), 2.44 (m, 2H, CH2), 3.48 (t, 1H, J=5.0 Hz, OTHP), 3.91 (t, 1H, J=10.0 Hz, OTHP), 4.80 (s, 1H, OTHP), 6.65 (d, 2H, J=5.0 Hz, Ar—H), 6.95 (d, 2H, J=10.0 Hz, Ar—H), 9.10 (s, 1H, NH), 10.87 (s, 1H, OH).

後処理

  1. extractionThe mixture was extracted with water
  2. dry with materialdried over magnesium sulfate
  3. customThe residue was purified by chromatography (MeOH:DCM=1:50)

出典と根拠

ORDレコード
ord-83fe9547861540b597c0b22ffdd833e6
出典データセット
uspto-grants-2012_08
特許番号
US08242282B2

反応ノート

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