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

Base Information

• Chemical Name: (S)-2-{(S)-3-(4-Benzyloxy-phenyl)-2-[(S)-2-tert-butoxycarbonylamino-3-(3,5-dichloro-4-hydroxy-phenyl)-propionylamino]-propionylamino}-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester
• CAS No.: 123418-33-7
• Molecular Formula: C₄₀H₄₁Br₂Cl₂N₃O₉
• Molecular Weight: 938.494

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

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

Chemical Property:

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

There total 4 articles about (S)-2-{(S)-3-(4-Benzyloxy-phenyl)-2-[(S)-2-tert-butoxycarbonylamino-3-(3,5-dichloro-4-hydroxy-phenyl)-propionylamino]-propionylamino}-3-(3,5-dibromo-4-hydroxy-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: 78.0%

N-t-butoxycarbonyl-3,5-dichloro-L-tyrosine (123418-41-7,1213365-16-2,1259972-62-7) + (S)-2-[(S)-2-Amino-3-(4-benzyloxy-phenyl)-propionylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester; hydrochloride (123418-32-6) → (S)-2-{(S)-3-(4-Benzyloxy-phenyl)-2-[(S)-2-tert-butoxycarbonylamino-3-(3,5-dichloro-4-hydroxy-phenyl)-propionylamino]-propionylamino}-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester (123418-33-7)

Guidance literature:

With 4-methyl-morpholine; 1,2,3-Benzotriazole; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; 0 deg C to room temp., overnight;

DOI:10.1016/S0040-4039(00)95207-9

Reference yield:

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3,54784-43-9) → (S)-2-{(S)-3-(4-Benzyloxy-phenyl)-2-[(S)-2-tert-butoxycarbonylamino-3-(3,5-dichloro-4-hydroxy-phenyl)-propionylamino]-propionylamino}-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester (123418-33-7)

Guidance literature:

Multi-step reaction with 3 steps

1: DCC, 1-hydroxybenztriazole, N-methylmorpholine / dimethylformamide / 0 deg C to room temp., overnight

2: HCl / dioxane / Ambient temperature; overnight

3: 78 percent / DCC, 1-hydrobenztriazole, N-methylmorpholine / dimethylformamide / 0 deg C to room temp., overnight

With 4-methyl-morpholine; hydrogenchloride; 1,2,3-Benzotriazole; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)95207-9

Reference yield:

3',5'-dibromo-L-tyrosine methyl ester (67470-21-7,173383-29-4) → (S)-2-{(S)-3-(4-Benzyloxy-phenyl)-2-[(S)-2-tert-butoxycarbonylamino-3-(3,5-dichloro-4-hydroxy-phenyl)-propionylamino]-propionylamino}-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester (123418-33-7)

Guidance literature:

Multi-step reaction with 3 steps

1: DCC, 1-hydroxybenztriazole, N-methylmorpholine / dimethylformamide / 0 deg C to room temp., overnight

2: HCl / dioxane / Ambient temperature; overnight

3: 78 percent / DCC, 1-hydrobenztriazole, N-methylmorpholine / dimethylformamide / 0 deg C to room temp., overnight

With 4-methyl-morpholine; hydrogenchloride; 1,2,3-Benzotriazole; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)95207-9

upstream raw materials:

N-t-butoxycarbonyl-3,5-dichloro-L-tyrosine

(S)-2-[(S)-2-Amino-3-(4-benzyloxy-phenyl)-propionylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester; hydrochloride

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

3',5'-dibromo-L-tyrosine methyl ester

Downstream raw materials:

(9S,12S,15S)-9-Acetylamino-4-hydroxy-12-(4-hydroxy-benzyl)-10,13-dioxo-2-oxa-11,14-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-15-carboxylic acid

(9S,12S,15S)-9-Acetylamino-4-hydroxy-12-(4-hydroxy-benzyl)-10,13-dioxo-2-oxa-11,14-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-15-carboxylic acid methyl ester

(9S,12S,15S)-9-tert-Butoxycarbonylamino-4-hydroxy-12-(4-hydroxy-benzyl)-10,13-dioxo-2-oxa-11,14-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-15-carboxylic acid methyl ester

(9S,12S,15S)-12-(4-Benzyloxy-benzyl)-19,20-dibromo-9-tert-butoxycarbonylamino-5-chloro-4-hydroxy-10,13-dioxo-2-oxa-11,14-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-15-carboxylic acid methyl ester

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