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

HRID 1416563Notes

Reaction equation

HRID 1416563 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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) δ0.91 (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.

Workup

  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)

Sources & evidence

ORD record
ord-6cb155b34aac49389e9769a345a95a18
Source dataset
uspto-grants-1999_06
Patent number
US05914332

Reaction notes

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