(S)-2-{(S)-3-(4-benzyloxyphenyl)-2-[(S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propionylamino]propionylamino}-3-[3-bromo-4-(2,2,2-trifluoroacetylamino)phenyl]propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-{(S)-3-(4-benzyloxyphenyl)-2-[(S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propionylamino]propionylamino}-3-[3-bromo-4-(2,2,2-trifluoroacetylamino)phenyl]propionic acid methyl ester
• CAS No.: 884302-83-4
• Molecular Formula: C₄₂H₄₄BrF₃N₄O₉
• Molecular Weight: 885.732

Synonyms:(S)-2-{(S)-3-(4-benzyloxyphenyl)-2-[(S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propionylamino]propionylamino}-3-[3-bromo-4-(2,2,2-trifluoroacetylamino)phenyl]propionic acid methyl ester

Chemical Property of (S)-2-{(S)-3-(4-benzyloxyphenyl)-2-[(S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propionylamino]propionylamino}-3-[3-bromo-4-(2,2,2-trifluoroacetylamino)phenyl]propionic acid methyl ester

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Technology Process of (S)-2-{(S)-3-(4-benzyloxyphenyl)-2-[(S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propionylamino]propionylamino}-3-[3-bromo-4-(2,2,2-trifluoroacetylamino)phenyl]propionic acid methyl ester

There total 2 articles about (S)-2-{(S)-3-(4-benzyloxyphenyl)-2-[(S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propionylamino]propionylamino}-3-[3-bromo-4-(2,2,2-trifluoroacetylamino)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:

(S)-3-(4-Benzyloxy-phenyl)-2-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-propionic acid (1027955-92-5) + (S)-2-Amino-3-[3-bromo-4-(2,2,2-trifluoro-acetylamino)-phenyl]-propionic acid methyl ester; compound with trifluoro-acetic acid → (S)-2-{(S)-3-(4-benzyloxyphenyl)-2-[(S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propionylamino]propionylamino}-3-[3-bromo-4-(2,2,2-trifluoroacetylamino)phenyl]propionic acid methyl ester (884302-83-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 14h;

DOI:10.1002/anie.200503538

Reference yield:

(S)-3-(4-Benzyloxy-phenyl)-2-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-propionic acid methyl ester → (S)-2-{(S)-3-(4-benzyloxyphenyl)-2-[(S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propionylamino]propionylamino}-3-[3-bromo-4-(2,2,2-trifluoroacetylamino)phenyl]propionic acid methyl ester (884302-83-4)

Guidance literature:

Multi-step reaction with 2 steps

1: LiOH / tetrahydrofuran; methanol; H₂O / 0.5 h / 0 °C

2: 358 mg / HATU; DIPEA / dimethylformamide / 14 h / 0 - 20 °C

With lithium hydroxide; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1002/anie.200503538

Reference yield: 52.0%

(S)-2-{(S)-3-(4-benzyloxyphenyl)-2-[(S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propionylamino]propionylamino}-3-[3-bromo-4-(2,2,2-trifluoroacetylamino)phenyl]propionic acid methyl ester (884302-83-4) → (9S,12S,15S)-12-(4-benzyloxybenzyl)-15-(tert-butoxycarbonylamino)-11,14-dioxo-4-(2,2,2-trifluoroacetylamino)-2-oxa-10,13-diaza-tricyclo[15.2.2.13,7]docosa-1(20),3(22),4,6,17(21),18-hexaene-9-carboxylic acid methyl ester (884302-84-5)

Guidance literature:

With copper(l) iodide; N,N-dimethylglycine hydrochoride; caesium carbonate; In 1,4-dioxane; at 20 ℃; for 24h;

DOI:10.1002/anie.200503538

upstream raw materials:

(S)-3-(4-Benzyloxy-phenyl)-2-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-propionic acid

Downstream raw materials:

(9S,12S,15S)-12-(4-benzyloxybenzyl)-15-(tert-butoxycarbonylamino)-11,14-dioxo-4-(2,2,2-trifluoroacetylamino)-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid methyl ester

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