Phosgene → 1-({4-(tert-Butyl-dimethyl-silanyloxy)-1-[hept-6-enyl-(4-methoxy-benzyl)-carbamoyl]-pyrrolidine-2-carbonyl}-amino)-2-vinyl-cyclopropanecarboxylic acid ethyl ester

Compound 124 (5.88 g, 15.4 mmol) was dissolved in THF (200 ml), NaHCO3 (s) (appr. 10 ml) was added followed by phosgene-solution (20% in toluene, 15.9 ml, 30.7 mmol). The reaction mixture was stirred vigorously for 1 h and then filtrated, evaporated and redissolved in DCM (200 ml). NaHCO3 (s) (appr. 10 ml) was added followed by hept-6-enyl-(4-methoxy-benzyl)-amine (5.58 g, 23.9 mmol). The reaction mixture was stirred at room temperature overnight, filtrated and evaporated on silica. The crude product was purified by column chromatography on silica (EtOAc/n-Heptane 25/75-50/50) to give the title compound (4.9 g, 50%).

1. filtrationfiltrated
2. customevaporated
3. dissolutionredissolved in DCM (200 ml)
4. additionNaHCO3 (s) (appr. 10 ml) was added
5. stirringThe reaction mixture was stirred at room temperature overnight
6. filtrationfiltrated
7. customevaporated on silica
8. customThe crude product was purified by column chromatography on silica (EtOAc/n-Heptane 25/75-50/50)

ORDレコード

ord-271cd91e78094bc9810efc0300140e51

出典データセット

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07666834B2