(S)-2-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetylamino)-3-(3-iodo-phenyl)-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetylamino)-3-(3-iodo-phenyl)-propionic acid methyl ester
• CAS No.: 371111-68-1
• Molecular Formula: C₂₃H₃₃IN₂O₅
• Molecular Weight: 544.43
• Mol file: 371111-68-1.mol

Synonyms:(S)-2-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetylamino)-3-(3-iodo-phenyl)-propionic acid methyl ester

Chemical Property of (S)-2-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetylamino)-3-(3-iodo-phenyl)-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetylamino)-3-(3-iodo-phenyl)-propionic acid methyl ester

There total 1 articles about (S)-2-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetylamino)-3-(3-iodo-phenyl)-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: 84.0%

L-(3-iodo)phenylalanine methyl ester hydrochloride + N-(tert-butoxycarbonyl)-L-cyclohexylglycine (109183-71-3) → (S)-2-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetylamino)-3-(3-iodo-phenyl)-propionic acid methyl ester (371111-68-1)

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; at -20 ℃;

DOI:10.1016/j.bmcl.2005.07.033

Reference yield:

(S)-2-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetylamino)-3-(3-iodo-phenyl)-propionic acid methyl ester (371111-68-1) → (S)-2-((S)-2-Amino-2-cyclohexyl-acetylamino)-3-(3-iodo-phenyl)-propionic acid methyl ester; hydrochloride

Guidance literature:

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

DOI:10.1016/j.bmcl.2005.07.033

Reference yield:

(S)-2-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetylamino)-3-(3-iodo-phenyl)-propionic acid methyl ester (371111-68-1) → (3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1(19),16(20),17-triene-3-carboxylic acid methyl ester (371111-73-8)

Guidance literature:

Multi-step reaction with 4 steps

1: HCl / dioxane / 20 °C

2: 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / -20 °C

3: 37 percent / Pd(PPh₃)4; Et₃N / acetonitrile; dimethylformamide / 80 °C

4: 100 percent / H₂ / Pd/C / ethanol / 20 °C

With 4-methyl-morpholine; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 3: Heck reaction;

DOI:10.1016/j.bmcl.2005.07.033

upstream raw materials:

N-(tert-butoxycarbonyl)-L-cyclohexylglycine

Downstream raw materials:

(E)-(3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,14,16⁽²⁰⁾,17-tetraene-3-carboxylic acid methyl ester

(E)-(3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,14,16⁽²⁰⁾,17-tetraene-3-carboxylic acid

(3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-3-carboxylic acid methyl ester

(S)-(2-{3-[((E)-(3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,14,16⁽²⁰⁾,17-tetraene-3-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid