[S,S]-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetylamino)-3-(3-hydroxyphenyl)propionic acid methyl ester

Base Information

• Chemical Name: [S,S]-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetylamino)-3-(3-hydroxyphenyl)propionic acid methyl ester
• CAS No.: 371111-41-0
• Molecular Formula: C₂₃H₃₄N₂O₆
• Molecular Weight: 434.533
• Mol file: 371111-41-0.mol

Synonyms:[S,S]-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetylamino)-3-(3-hydroxyphenyl)propionic acid methyl ester

Chemical Property of [S,S]-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetylamino)-3-(3-hydroxyphenyl)propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [S,S]-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetylamino)-3-(3-hydroxyphenyl)propionic acid methyl ester

There total 1 articles about [S,S]-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetylamino)-3-(3-hydroxyphenyl)propionic acid methyl 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: 88.0%

N-(tert-butoxycarbonyl)-L-cyclohexylglycine (109183-71-3) + methyl (2S)-2-amino-3-(3-hydroxyphenyl)propanoate hydrochloride (34260-70-3,34260-72-5,72683-79-5) → [S,S]-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetylamino)-3-(3-hydroxyphenyl)propionic acid methyl ester (371111-41-0)

Guidance literature:

With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; In dichloromethane; N,N-dimethyl-formamide; for 18.5h; cooling;

DOI:10.1021/jm050323b

Reference yield: 96.0%

[S,S]-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetylamino)-3-(3-hydroxyphenyl)propionic acid methyl ester (371111-41-0) → (S,S)-C-cyclohexyl-C-[2-(3-hydroxyphenyl)-1-methoxycarbonylethoxycarbamoyl]methyl ammonium chloride

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 2h;

DOI:10.1021/jm0489556

Reference yield:

[S,S]-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetylamino)-3-(3-hydroxyphenyl)propionic acid methyl ester (371111-41-0) → {3-[((9S,12S,15S)-15-tert-Butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.13,7]docosa-1(20),3,5,7(22),17(21),18-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetic acid

Guidance literature:

Multi-step reaction with 5 steps

1.1: 96 percent / HCl / dioxane / 2 h / 20 °C

2.1: HOBt; Huenigs base; EDCI / CH₂Cl₂

2.2: CH₂Cl₂ / cooling

3.1: Dess-Martin periodinane / CH₂Cl₂; tetrahydrofuran

4.1: H₂ / Pd/C / ethyl acetate

With hydrogenchloride; hydrogen; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; ethyl acetate; 4.1: Dess-Martin oxidation;

DOI:10.1021/jm0489556

upstream raw materials:

N-(tert-butoxycarbonyl)-L-cyclohexylglycine

methyl (2S)-2-amino-3-(3-hydroxyphenyl)propanoate hydrochloride

Downstream raw materials:

10-cyclohexyl-8,11-dioxo-2-oxa-9,12-diazabicyclo[13.3.1]nonadeca-1⁽¹⁹⁾,15,17-triene-13-carboxylic acid

10-cyclohexyl-8,11-dioxo-2-oxa-9,12-diazabicyclo[13.3.1]nonadeca-1⁽¹⁹⁾,15,17-triene-13-carboxylic acid methyl ester

methyl 11(S)-cyclohexyl-9,12-dioxo-2-oxa-10,13-diazabicyclo[14.3.1]eicosa-1⁽²⁰⁾,16,18-triene-14(S)-carboxylate

11(S)-cyclohexyl-9,12-dioxo-2-oxa-10,13-diazabicyclo[14.3.1]eicosa-1⁽²⁰⁾,16,18-triene-14(S)-carboxylic acid