Methyl Acrylate → N-(3-Methoxy-3-oxopropyl)-L-valine tert-Butyl Ester

HRID 428480

反応式

HRID 428480 の反応式
[C:1]([O:5][C:6](=[O:12])[C@H:7]([CH:9]([CH3:11])[CH3:10])[NH2:8])([CH3:4])([CH3:3])[CH3:2].[C:13]([O:17][CH3:18])(=[O:16])[CH:14]=[CH2:15]>CO>[C:1]([O:5][C:6](=[O:12])[C@H:7]([CH:9]([CH3:10])[CH3:11])[NH:8][CH2:15][CH2:14][C:13]([O:17][CH3:18])=[O:16])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 7294Methyl Acrylate2 回HCID 114626tert-Butyl L-valinate

生成物 1

HCID 21309732N-(3-Methoxy-3-oxopropyl)-L-valine tert-Butyl Ester収率 93.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 1.73 g of L-Valine t-butyl ester in 10 ml of methanol was added 9.0 ml of methyl acrylate. The solution was heated to reflux overnight. Another 9.0 ml of methyl acrylate was added and continued the reflux for 24 h. The solvent was evaporated in vacuo and the crude product was purified by silica gel column chromatography (20% ethyl acetate in hexane) to provide 2.435 g of desired compound (93.9%). 300 MHz 1H NMR (CDCl3) δ 0.91 (d, J=3.5 Hz, 3H), 0.93 (d, J=3.5 Hz, 3H), 1.47 (s, 9H), 1.85 (m, 1H), 2.47 (t, J=7 Hz, 2H), 2.68 (m, 1H), 2.81 (d, J=6 Hz, 1H), 2.95 (m, 1H), 3.68 (s, 3H). Mass spectrum: (M+H)+=260.

後処理

  1. temperatureThe solution was heated
  2. temperatureto reflux overnight
  3. temperaturereflux for 24 h
  4. customThe solvent was evaporated in vacuo
  5. customthe crude product was purified by silica gel column chromatography (20% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-06d9abc515b0413c848401be791d3a51
出典データセット
uspto-grants-2001_11
特許番号
US06313296B1

関連ノート

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