(S)-(4-cyanophenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-acetic acid (1R,2S,5R)-menthyl ester

Base Information

Chemical Name:(S)-(4-cyanophenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-acetic acid (1R,2S,5R)-menthyl ester
CAS No.:450844-55-0
Molecular Formula:C₂₃H₂₉N₃O₃
Molecular Weight:395.502
Hs Code.:

Synonyms:(S)-(4-cyanophenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-acetic acid (1R,2S,5R)-menthyl ester

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Chemical Property of (S)-(4-cyanophenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-acetic acid (1R,2S,5R)-menthyl ester

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Technology Process of (S)-(4-cyanophenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-acetic acid (1R,2S,5R)-menthyl ester

There total 3 articles about (S)-(4-cyanophenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-acetic acid (1R,2S,5R)-menthyl 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: 68.0%

: 450844-51-6
(4-cyanophenyl)-2-oxo-acetic acid (1R,2S,5R)-menthyl ester

: 71759-88-1
5-iodo-1N-methyl imidazole

: 450844-55-0
(S)-(4-cyanophenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-acetic acid (1R,2S,5R)-menthyl ester

Guidance literature:: 5-iodo-1N-methyl imidazole; With chloro-trimethyl-silane; ethylene dibromide; zinc; In tetrahydrofuran; Heating;

(4-cyanophenyl)-2-oxo-acetic acid (1R,2S,5R)-menthyl ester; With magnesium bromide; In tetrahydrofuran; at 25 ℃;
DOI:10.1016/j.tet.2005.02.072

Reference yield:

: 2216-51-5
(-)-menthol

: 450844-55-0
(S)-(4-cyanophenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-acetic acid (1R,2S,5R)-menthyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: titanium(IV) ethoxide / xylene / 8 h / 80 °C

1.2: 79 percent / acetic anhydride / xylene / 12 h / 80 °C

2.1: zinc; 1,2-dibromoethane; chlorotrimethylsilane / tetrahydrofuran / Heating

2.2: 68 percent / MgBr₂-OEt₂ / tetrahydrofuran / 25 °C

With chloro-trimethyl-silane; ethylene dibromide; zinc; titanium(IV) tetraethanolate; In tetrahydrofuran; xylene;
DOI:10.1016/j.tet.2005.02.072

Reference yield:

: 302912-31-8
ethyl-4-cyanobenzoylformate

: 450844-55-0
(S)-(4-cyanophenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-acetic acid (1R,2S,5R)-menthyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: titanium(IV) ethoxide / xylene / 8 h / 80 °C

1.2: 79 percent / acetic anhydride / xylene / 12 h / 80 °C

2.1: zinc; 1,2-dibromoethane; chlorotrimethylsilane / tetrahydrofuran / Heating

2.2: 68 percent / MgBr₂-OEt₂ / tetrahydrofuran / 25 °C

With chloro-trimethyl-silane; ethylene dibromide; zinc; titanium(IV) tetraethanolate; In tetrahydrofuran; xylene;
DOI:10.1016/j.tet.2005.02.072