Reaktion #313149

Reaktionsgleichung

dioxane

ammonia

[(2S,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl]acetic acid

intermediate 7

[(2S,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl]acetic acid

HOBt

EDC

→

2-[(2S,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl]acetamide

Ausbeute 81.0%

Lösungsmittel

Ethyl acetate

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Waschenthe organic phase was washed with citric acid 5%, NH4Cl, NaHCO3
3. 3
   TrocknenThe organic phase was dried (MgSO4)
4. 4
   Einengenconcentrated

Vorschrift

To a solution of [(2S,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl]acetic acid (intermediate 7, 50 mg, 0.14 mmol) in tetrahydrofuran (4 ml) were added HOBt (29 mg, 0.21 mmol), EDC (41 mg, 0.21 mmol), DMAP (2 mg, 0.01 mmol) followed by ammonia in dioxane (0.425 ml, 2M, 0.21 mmol). The reaction mixture was stirred overnight Ethyl acetate was added and the organic phase was washed with citric acid 5%, NH4Cl, NaHCO3 then brine. The organic phase was dried (MgSO4) and concentrated to afford 2-[(2S,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl]acetamide (40 mg). Yield: 81%. HPLC purity: 93%

Quelle