(2S)-2-(5'-tert-butoxycarbonyl-2'-methylphenyl)-2-(dimethylamino)acetic acid (-)-8-phenylmenthol ester

Base Information

• Chemical Name: (2S)-2-(5'-tert-butoxycarbonyl-2'-methylphenyl)-2-(dimethylamino)acetic acid (-)-8-phenylmenthol ester
• CAS No.: 1004759-69-6
• Molecular Formula: C₃₂H₄₅NO₄
• Molecular Weight: 507.714

Synonyms:(2S)-2-(5'-tert-butoxycarbonyl-2'-methylphenyl)-2-(dimethylamino)acetic acid (-)-8-phenylmenthol ester

Chemical Property of (2S)-2-(5'-tert-butoxycarbonyl-2'-methylphenyl)-2-(dimethylamino)acetic acid (-)-8-phenylmenthol ester

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Technology Process of (2S)-2-(5'-tert-butoxycarbonyl-2'-methylphenyl)-2-(dimethylamino)acetic acid (-)-8-phenylmenthol ester

There total 2 articles about (2S)-2-(5'-tert-butoxycarbonyl-2'-methylphenyl)-2-(dimethylamino)acetic acid (-)-8-phenylmenthol ester 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: 95.0%

N-(4'-tert-butoxycarbonylbenzyl)-N,N-dimethyl-N-[(-)-8-phenylmenthoyloxycarbonylmethyl]ammonium bromide (1004759-63-0) → (2S)-2-(5'-tert-butoxycarbonyl-2'-methylphenyl)-2-(dimethylamino)acetic acid (-)-8-phenylmenthol ester (1004759-69-6)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at -40 ℃; for 4h;

DOI:10.1002/anie.200703832

Reference yield: 49.0%

N-(4'-tert-butoxycarbonylbenzyl)-N,N-dimethyl-N-[(-)-8-phenylmenthoyloxycarbonylmethyl]ammonium bromide (1004759-63-0) → C32H45NO4 + (2R)-2-(5'-tert-butoxycarbonyl-2'-methylphenyl)-2-(dimethylamino)acetic acid (-)-8-phenylmenthol ester + (2S)-2-(5'-tert-butoxycarbonyl-2'-methylphenyl)-2-(dimethylamino)acetic acid (-)-8-phenylmenthol ester (1004759-69-6)

Guidance literature:

With potassium hydroxide; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1002/anie.200703832

Reference yield: 97.0%

(2S)-2-(5'-tert-butoxycarbonyl-2'-methylphenyl)-2-(dimethylamino)acetic acid (-)-8-phenylmenthol ester (1004759-69-6) + 4-cyanobenzyl bromide (17201-43-3) → N-{(S)-(5'-tert-butoxycarbonyl-2'-methylphenyl)[(-)-8-phenylmenthyloxycarbonyl]methyl}-N-(4''-cyanobenzyl)-N,N-dimethylammonium bromide (1088481-76-8)

Guidance literature:

In acetonitrile; at 20 ℃;

DOI:10.1039/b811162f

upstream raw materials:

N-(4'-tert-butoxycarbonylbenzyl)-N,N-dimethyl-N-[(-)-8-phenylmenthoyloxycarbonylmethyl]ammonium bromide

Downstream raw materials:

N-[(Z)-but-2-en-1-yl]-N-{(S)-(5'-tert-butoxycarbonyl-2'-methylphenyl)[(-)-8-phenylmenthyloxycarbonyl]methyl}-N,N-dimethylammonium bromide

N-[(E)-but-2-en-1-yl]-N-{(S)-(5'-tert-butoxycarbonyl-2'-methylphenyl)[(-)-8-phenylmenthyloxycarbonyl]methyl}-N,N-dimethylammonium bromide

N-{(S)-(5'-tert-butoxycarbonyl-2'-methylphenyl)[(-)-8-phenylmenthyloxycarbonyl]methyl}-N,N-dimethyl-N-(2-methylprop-2-en-1-yl)ammonium bromide

N-allyl-N-{(S)-(5'-tert-butoxycarbonyl-2'-methylphenyl)[(-)-8-phenylmenthyloxycarbonyl]methyl}-N,N-dimethylammonium bromide

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