(S)-N-(4-methoxyphenyl)-3,4-dihydroxy-3,4-O-isopropylidenebutanamide

Base Information

• Chemical Name: (S)-N-(4-methoxyphenyl)-3,4-dihydroxy-3,4-O-isopropylidenebutanamide
• CAS No.: 264903-63-1
• Molecular Formula: C₁₄H₁₉NO₄
• Molecular Weight: 265.309

Synonyms:(S)-N-(4-methoxyphenyl)-3,4-dihydroxy-3,4-O-isopropylidenebutanamide

Chemical Property of (S)-N-(4-methoxyphenyl)-3,4-dihydroxy-3,4-O-isopropylidenebutanamide

Chemical Property:

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Technology Process of (S)-N-(4-methoxyphenyl)-3,4-dihydroxy-3,4-O-isopropylidenebutanamide

There total 2 articles about (S)-N-(4-methoxyphenyl)-3,4-dihydroxy-3,4-O-isopropylidenebutanamide 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: 86.0%

4-methoxy-aniline (104-94-9) + (S)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetic acid (87319-12-8) → (S)-N-(4-methoxyphenyl)-3,4-dihydroxy-3,4-O-isopropylidenebutanamide (264903-63-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃;

DOI:10.3987/com-99-8805

Reference yield:

methyl (3S)-3,4-O-isopropylidene-3,4-dihydroxybutanoate (95422-24-5) → (S)-N-(4-methoxyphenyl)-3,4-dihydroxy-3,4-O-isopropylidenebutanamide (264903-63-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / aq. NaOH / acetone / 0.75 h / 0 - 20 °C

2: 86 percent / DMAP; DCC / CH₂Cl₂ / 0 - 20 °C

With dmap; sodium hydroxide; dicyclohexyl-carbodiimide; In dichloromethane; acetone;

DOI:10.3987/com-99-8805

Reference yield: 98.0%

(S)-N-(4-methoxyphenyl)-3,4-dihydroxy-3,4-O-isopropylidenebutanamide (264903-63-1) → [2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-(4-methoxy-phenyl)-amine (264903-64-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 17h; Heating;

DOI:10.3987/com-99-8805

upstream raw materials:

4-methoxy-aniline

(S)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetic acid

methyl (3S)-3,4-O-isopropylidene-3,4-dihydroxybutanoate

Downstream raw materials:

[2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-(4-methoxy-phenyl)-amine

(4R)-4-butyl-1-(4-methoxyphenyl)pyrrolidin-2-one

1-(4-Methoxy-phenyl)-4-(S)-oxiranyl-pyrrolidin-2-one

4-((S)-1,2-Dihydroxy-ethyl)-1-(4-methoxy-phenyl)-pyrrolidin-2-one

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