ChemicalBook CAS DataBase List Oxyepiberberine

Oxyepiberberine synthesis

6synthesis methods

Product Name:Oxyepiberberine
CAS Number:19716-60-0
Molecular formula:C20H17NO5
Molecular Weight:351.35

131543-46-9 Synthesis

131543-46-9
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Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

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19716-60-0
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Yield: 21%

Reaction Conditions:

with copper(II) sulfate;acetic acid in water for 3 h;Reflux;

Steps:

8.49
To a solution of 150 mg (0.48 mmol) of C in 2 mL of AcOH was added 1.0 g of CuS04, followed 2 mL of aqueous (30%) glyoxal. The reaction mixture was heated to reflux for 3 hours. The most solvent was removed under vacuum, and then extracted with EtOAc. The organic phase was washed with water, brine and dried over anhydrous NaSC The solvent was removed under vacuum, the crude product was purified with column chromatograph eluting with EA: MeOH = 20: 1. 35 mg of the title compound was obtained. Yield: 21.0%. NMR (CDCb, 300 MHz) 5= 8.81 (s, 1H), 8.41(br, 1H), 7.99 (d, J= 8.7 Hz), 7.51 (d, J= 8.7 Hz), 6.94 (s, 1H), 6.35 (s, 2H), 4.66 (t, J= 5.7 Hz, 2H), 3.81 (s, 3H), 3.78 (s, 3H), 3.06 (t, J = 6.2 Hz, 2H). MS: m/z (APCI-ESI): 352.1(M⁺+1).

References:

LIU, Jingwen;CVI PHARMACEUTICALS LIMITED WO2021/67490, 2021, A1 Location in patent:Page/Page column 95; 96

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19716-60-0
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References