(R)-tert-Butoxycarbonylamino-(3,5-dibromo-4-hydroxy-phenyl)-acetic acid

Base Information

• Chemical Name: (R)-tert-Butoxycarbonylamino-(3,5-dibromo-4-hydroxy-phenyl)-acetic acid
• CAS No.: 123593-47-5
• Molecular Formula: C₁₃H₁₅Br₂NO₅
• Molecular Weight: 425.074
• Mol file: 123593-47-5.mol

Synonyms:(R)-tert-Butoxycarbonylamino-(3,5-dibromo-4-hydroxy-phenyl)-acetic acid

Chemical Property of (R)-tert-Butoxycarbonylamino-(3,5-dibromo-4-hydroxy-phenyl)-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-tert-Butoxycarbonylamino-(3,5-dibromo-4-hydroxy-phenyl)-acetic acid

There total 4 articles about (R)-tert-Butoxycarbonylamino-(3,5-dibromo-4-hydroxy-phenyl)-acetic 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: 90.0%

methyl (2R)-2-(3,5-dibromo-4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate → (R)-tert-Butoxycarbonylamino-(3,5-dibromo-4-hydroxy-phenyl)-acetic acid (123593-47-5)

Guidance literature:

methyl (2R)-2-(3,5-dibromo-4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate; With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 25 ℃; for 16h;

With hydrogenchloride; In water; pH=4;

DOI:10.1021/acs.jmedchem.1c00034

Reference yield:

D-4-hydroxyphenylglycine (22818-40-2) + tert-Butyl pyrocarbonate (120916-43-0) → (R)-tert-Butoxycarbonylamino-(3,5-dibromo-4-hydroxy-phenyl)-acetic acid (123593-47-5)

Guidance literature:

With bromine; Yield given. Multistep reaction; 1.) acetic acid, 2.) aq. dioxane;

DOI:10.1021/ja00206a021

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (R)-tert-Butoxycarbonylamino-(3,5-dibromo-4-hydroxy-phenyl)-acetic acid (123593-47-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogen bromide; bromine / acetic acid / 16 h / 25 °C

1.2: pH 14

1.3: 16 h / 25 °C

2.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 16 h / 25 °C

2.2: pH 4

With lithium hydroxide monohydrate; hydrogen bromide; bromine; In tetrahydrofuran; water; acetic acid;

DOI:10.1021/acs.jmedchem.1c00034

upstream raw materials:

D-4-hydroxyphenylglycine

tert-Butyl pyrocarbonate

di-tert-butyl dicarbonate

D-2-p-hydroxyphenylglycine methyl ester

Downstream raw materials:

C₅₈H₅₉Cl₄N₇O₁₅

(8R,11R,14S,15R)-11-(4-Benzyloxy-phenyl)-5-bromo-8-tert-butoxycarbonylamino-18,19-dichloro-15-hydroxy-7-methoxy-4,9,12-trioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,5,16⁽²⁰⁾,17-pentaene-14-carboxylic acid methyl ester

(2S,3R)-2-{(R)-2-(4-Benzyloxy-phenyl)-2-[(R)-2-tert-butoxycarbonylamino-2-(3,5-dibromo-4-hydroxy-phenyl)-acetylamino]-acetylamino}-3-(3,5-dichloro-4-hydroxy-phenyl)-3-hydroxy-propionic acid methyl ester

(8R,11R,14S,15R)-11-(4-Benzyloxy-phenyl)-5-bromo-8-tert-butoxycarbonylamino-18,19-dichloro-4,15-dihydroxy-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,4,6,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester