(+)-3-<(2-amino-1-naphthalenyl)thio>-2-hydroxy-3-(4-methoxyphenyl)propanoic acid

Base Information

• Chemical Name: (+)-3-<(2-amino-1-naphthalenyl)thio>-2-hydroxy-3-(4-methoxyphenyl)propanoic acid
• CAS No.: 125226-69-9
• Molecular Formula: C₂₀H₁₉NO₄S
• Molecular Weight: 369.441

Synonyms:(+)-3-<(2-amino-1-naphthalenyl)thio>-2-hydroxy-3-(4-methoxyphenyl)propanoic acid

Chemical Property of (+)-3-<(2-amino-1-naphthalenyl)thio>-2-hydroxy-3-(4-methoxyphenyl)propanoic acid

Chemical Property:

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Technology Process of (+)-3-<(2-amino-1-naphthalenyl)thio>-2-hydroxy-3-(4-methoxyphenyl)propanoic acid

There total 2 articles about (+)-3-<(2-amino-1-naphthalenyl)thio>-2-hydroxy-3-(4-methoxyphenyl)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: 94.5%

(2R,3S)-3-<(2-amino-1-naphthalenyl)thio>-2-hydroxy-3-(4-methoxyphenyl)propanoic acid (1R,2S)-2-phenylcyclohexyl ester hydrochloride (128232-04-2) → (+)-3-<(2-amino-1-naphthalenyl)thio>-2-hydroxy-3-(4-methoxyphenyl)propanoic acid (125226-69-9)

Guidance literature:

With sodium hydroxide; In ethanol; 1.) 4 h, reflux, 2.) RT, overnight;

DOI:10.1021/jo00029a013

Reference yield:

2-aminonaphthalene-1-thiol (53338-20-8) → (+)-3-<(2-amino-1-naphthalenyl)thio>-2-hydroxy-3-(4-methoxyphenyl)propanoic acid (125226-69-9)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 20 h / Heating

2: 94.5 percent / 2 N NaOH / ethanol / 1.) 4 h, reflux, 2.) RT, overnight

With sodium hydroxide; In ethanol; toluene;

DOI:10.1021/jo00029a013

Reference yield: 85.0%

(+)-3-<(2-amino-1-naphthalenyl)thio>-2-hydroxy-3-(4-methoxyphenyl)propanoic acid (125226-69-9) → (2S,3S)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)naphtho[1,2-b][1,4]thiazepin-4(5H)-one (125276-26-8)

Guidance literature:

With toluene-4-sulfonic acid; In xylene; for 19h; Heating;

DOI:10.1021/jo00029a013

upstream raw materials:

(2R,3S)-3-<(2-amino-1-naphthalenyl)thio>-2-hydroxy-3-(4-methoxyphenyl)propanoic acid (1R,2S)-2-phenylcyclohexyl ester hydrochloride

2-aminonaphthalene-1-thiol

Downstream raw materials:

(2S,3S)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)naphtho[1,2-b][1,4]thiazepin-4(5H)-one

(+)-cis-3-(acetyloxy)-2,3-dihydro-2-(4-methoxyphenyl)-5-<2-(dimethylamino)ethyl>naphtho<1,2-b><1,4>thiazepin-4(5H)-one hydrochloride

(2S,3S)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-5-[2-(dimethylamino)ethyl]naphtho[1,2-b][1,4]thiazepin-4(5H)-one

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