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

HRID 428480

반응식

HRID 428480 반응식
[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]

참가 물질

4

반응물 2

HCID 7294Methyl Acrylate2회HCID 114626tert-Butyl L-valinate

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-06d9abc515b0413c848401be791d3a51
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313296B1

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