Diisopropylethylamine → {(R)-1-[Allyl-(2,4-dimethoxy-benzyl)-carbamoyl]-but-3-enyl}-carbamic acid tert-butyl ester

(R)-N-Boc-allylglycine (2.3 g, 9.9 mmol) was dissolved in dimethylformamide (20 ml) and activated with the coupling reagent TATU (3.5 g, 10.9 mmol) and Hünig's base (3.8 ml, 21.9 mmol) for 2 min. Allyl-(2,4-dimethoxy-benzyl)-amine (2.1 g, 9.9 mmol) dissolved in dimethylformamide (20 ml) was added to the chilled (ice-water bath) reaction mixture and the stirring was continued overnight. The solvent was evaporated and the residue was dissolved in ethyl acetate, washed with saturated NaHCO3 solution, 1 M KHSO4 solution, brine, dried (MgSO4.2H2O), filtered and concentrated under reduce pressure and purified over silica gel (ethyl acetate/n-heptane 1:4): colorless gum 2.6 g (62%);

1. additionwas added to the
2. temperaturechilled
3. customThe solvent was evaporated
4. dissolutionthe residue was dissolved in ethyl acetate
5. washwashed with saturated NaHCO3 solution, 1 M KHSO4 solution, brine
6. dry with materialdried (MgSO4.2H2O)
7. filtrationfiltered
8. concentrationconcentrated
9. custompurified over silica gel (ethyl acetate/n-heptane 1:4)

ORDレコード

ord-8c66eddc371c43c7a53c3ee05b304da1

出典データセット

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07501406B2