(E,S)-N-(3-ethoxycarbonyl-2-propenyl)-N-(1-phenylethyl)-3-oxobutanamide

Base Information

• Chemical Name: (E,S)-N-(3-ethoxycarbonyl-2-propenyl)-N-(1-phenylethyl)-3-oxobutanamide
• CAS No.: 224645-78-7
• Molecular Formula: C₁₈H₂₃NO₄
• Molecular Weight: 317.385
• Mol file: 224645-78-7.mol

Synonyms:(E,S)-N-(3-ethoxycarbonyl-2-propenyl)-N-(1-phenylethyl)-3-oxobutanamide

Chemical Property of (E,S)-N-(3-ethoxycarbonyl-2-propenyl)-N-(1-phenylethyl)-3-oxobutanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E,S)-N-(3-ethoxycarbonyl-2-propenyl)-N-(1-phenylethyl)-3-oxobutanamide

There total 1 articles about (E,S)-N-(3-ethoxycarbonyl-2-propenyl)-N-(1-phenylethyl)-3-oxobutanamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 77.0%

4-methyleneoxetan-2-one (674-82-8,2130-41-8) + (S)-N-<3-ethoxycarbonyl-2(E)-propen-1-yl>-N-(1-phenyleth-1-yl)amine (171196-82-0) → (E,S)-N-(3-ethoxycarbonyl-2-propenyl)-N-(1-phenylethyl)-3-oxobutanamide (224645-78-7)

Guidance literature:

With dmap; In tetrahydrofuran; at -15 ℃; for 1h;

DOI:10.1016/S0040-4020(99)00091-5

Reference yield: 71.0%

(E,S)-N-(3-ethoxycarbonyl-2-propenyl)-N-(1-phenylethyl)-3-oxobutanamide (224645-78-7) → ethyl (3S,4R,1'S)-<3-acetyl-2-oxo-1-(1'-phenylethyl)pyrrolidin-4-yl>acetate (224645-90-3) + ethyl (3R,4S,1'S)-<3-acetyl-2-oxo-1-(1'-phenylethyl)pyrrolidin-4-yl>acetate

Guidance literature:

With sodium ethanolate; In ethanol; at -78 ℃; for 1h; further reagent;

DOI:10.1016/S0040-4020(99)00091-5

Reference yield:

(E,S)-N-(3-ethoxycarbonyl-2-propenyl)-N-(1-phenylethyl)-3-oxobutanamide (224645-78-7) → ethyl (3S,4R,1'S,1''R)-<3-(1''-p-iodobenzoyloxyethyl)-2-oxo-1-(1'-phenylethyl)pyrrolidin-4-yl>acetate

Guidance literature:

Multi-step reaction with 3 steps

1: NaH / tetrahydrofuran / 1 h / -78 °C

2: KBH₄ / methanol / 1 h / -15 °C

3: 64 percent / Et₃N, DMAP / ethyl acetate / 12 h / Ambient temperature

With dmap; potassium borohydride; sodium hydride; triethylamine; In tetrahydrofuran; methanol; ethyl acetate;

DOI:10.1016/S0957-4166(99)00031-2

upstream raw materials:

4-methyleneoxetan-2-one

(S)-N-<3-ethoxycarbonyl-2(E)-propen-1-yl>-N-(1-phenyleth-1-yl)amine

Downstream raw materials:

ethyl (3S,4R,1'S)-<3-acetyl-2-oxo-1-(1'-phenylethyl)pyrrolidin-4-yl>acetate

ethyl (3S,4S,1'S,1''S)-<3-(1''-hydroxyethyl)-2-oxo-1-(1'-phenylethyl)pyrrolidin-4-yl>acetate

ethyl (3S,4S,1'S,1''R)-<3-(1''-hydroxyethyl)-2-oxo-1-(1'-phenylethyl)pyrrolidin-4-yl>acetate