(S)-2-acetamido-3-(4-hydroxy-3-(3-methylbut-2-enyl)phenyl)propanoic acid

Base Information

• Chemical Name: (S)-2-acetamido-3-(4-hydroxy-3-(3-methylbut-2-enyl)phenyl)propanoic acid
• CAS No.: 1075238-11-7
• Molecular Formula: C₁₆H₂₁NO₄
• Molecular Weight: 291.347

Synonyms:(S)-2-acetamido-3-(4-hydroxy-3-(3-methylbut-2-enyl)phenyl)propanoic acid

Chemical Property of (S)-2-acetamido-3-(4-hydroxy-3-(3-methylbut-2-enyl)phenyl)propanoic acid

Chemical Property:

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Technology Process of (S)-2-acetamido-3-(4-hydroxy-3-(3-methylbut-2-enyl)phenyl)propanoic acid

There total 3 articles about (S)-2-acetamido-3-(4-hydroxy-3-(3-methylbut-2-enyl)phenyl)propanoic acid 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: 69.0%

(S)-methyl 2-acetamido-3-(4-acetoxy-3-(3-methylbut-2-enyl)phenyl)propanoate → (S)-2-acetamido-3-(4-hydroxy-3-(3-methylbut-2-enyl)phenyl)propanoic acid (1075238-11-7)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; methanol; water; at 20 ℃; for 3h;

DOI:10.1080/00397911.2014.974614

Reference yield:

C15H19NO4 → (S)-2-acetamido-3-(4-hydroxy-3-(3-methylbut-2-enyl)phenyl)propanoic acid (1075238-11-7)

Guidance literature:

Multi-step reaction with 4 steps

1: N,N-dimethyl-aniline / 2 h / 250 °C / Microwave irradiation; Inert atmosphere

2: triethylamine / dichloromethane / 2 h / 0 - 20 °C

3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / 20 °C / Inert atmosphere

4: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 3 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lithium hydroxide monohydrate; N,N-dimethyl-aniline; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 1: |Claisen Rearrangement / 3: |Cross Metathesis;

DOI:10.1080/00397911.2014.974614

Reference yield:

(S)-methyl 2-acetamido-3-(3-allyl-4-hydroxyphenyl)propanoate → (S)-2-acetamido-3-(4-hydroxy-3-(3-methylbut-2-enyl)phenyl)propanoic acid (1075238-11-7)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 2 h / 0 - 20 °C

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / 20 °C / Inert atmosphere

3: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 3 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lithium hydroxide monohydrate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 2: |Cross Metathesis;

DOI:10.1080/00397911.2014.974614

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