(S)-2-(4-methoxyphenyl)-2-pivalamidoacetic acid

Base Information

• Chemical Name: (S)-2-(4-methoxyphenyl)-2-pivalamidoacetic acid
• CAS No.: 170688-64-9
• Molecular Formula: C₁₄H₁₉NO₄
• Molecular Weight: 265.309

Synonyms:

Chemical Property of (S)-2-(4-methoxyphenyl)-2-pivalamidoacetic acid

Chemical Property:

Purity/Quality:

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Technology Process of (S)-2-(4-methoxyphenyl)-2-pivalamidoacetic acid

There total 2 articles about (S)-2-(4-methoxyphenyl)-2-pivalamidoacetic 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:

2-(4-methoxyphenyl)-2-pivalamidoacetic acid + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → (S)-2-(4-methoxyphenyl)-2-pivalamidoacetic acid (170688-64-9) + (R,E)-2-(4-methoxy-2-(3-methoxy-3-oxoprop-1-en-1-yl)phenyl)-2-pivalamidoacetic acid + (S,E)-2-(4-methoxy-2-(3-methoxy-3-oxoprop-1-en-1-yl)phenyl)-2-pivalamidoacetic acid + (R)-2-(4-methoxyphenyl)-2-pivalamidoacetic acid

Guidance literature:

With oxygen; palladium diacetate; potassium hydrogencarbonate; (2S,3R)-3-(benzoyloxy)-2-((tert-butoxycarbonyl)amino)butanoic acid; In tert-Amyl alcohol; at 40 ℃; under 760.051 Torr; enantioselective reaction; Schlenk technique;

DOI:10.1002/anie.201510808

Reference yield:

2-(4-methoxyphenyl)glycine (2540-53-6,19789-59-4) + pivaloyl chloride (3282-30-2) → (S)-2-(4-methoxyphenyl)-2-pivalamidoacetic acid (170688-64-9) + (R,E)-2-(4-methoxy-2-(3-methoxy-3-oxoprop-1-en-1-yl)phenyl)-2-pivalamidoacetic acid + (S,E)-2-(4-methoxy-2-(3-methoxy-3-oxoprop-1-en-1-yl)phenyl)-2-pivalamidoacetic acid + (R)-2-(4-methoxyphenyl)-2-pivalamidoacetic acid

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / water / 8 h / 20 °C

2: palladium diacetate; potassium hydrogencarbonate; oxygen; (2S,3R)-3-(benzoyloxy)-2-((tert-butoxycarbonyl)amino)butanoic acid / tert-Amyl alcohol / 40 °C / 760.05 Torr / Schlenk technique

With oxygen; palladium diacetate; potassium hydrogencarbonate; (2S,3R)-3-(benzoyloxy)-2-((tert-butoxycarbonyl)amino)butanoic acid; sodium hydroxide; In tert-Amyl alcohol; water;

DOI:10.1002/anie.201510808

Reference yield:

(S)-2-(4-methoxyphenyl)-2-pivalamidoacetic acid (170688-64-9) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) + N-methylaniline (100-61-8) → (S)-α-[N-[(1,1-dimethylethyl)carbonyl]amino]-4-methoxy-N-methyl-N-phenylbenzeneacetamide (170688-68-3)

Guidance literature:

In dichloromethane;

upstream raw materials:

2-(4-methoxyphenyl)glycine

pivaloyl chloride

acrylic acid methyl ester

Downstream raw materials:

(S)-α-[N-[(1,1-dimethylethyl)carbonyl]amino]-4-methoxy-N-methyl-N-phenylbenzeneacetamide

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