15-(S)-tert-butoxycarbonylamino-4-methoxy-12-(S)-(4-methoxybenzyl)-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.1(3,7)]-docosa-1-⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-(S)-carboxylic acid methyl ester

Base Information

• Chemical Name: 15-(S)-tert-butoxycarbonylamino-4-methoxy-12-(S)-(4-methoxybenzyl)-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.1(3,7)]-docosa-1-⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-(S)-carboxylic acid methyl ester
• CAS No.: 192315-55-2
• Molecular Formula: C₃₅H₄₁N₃O₉
• Molecular Weight: 647.725
• Mol file: 192315-55-2.mol

Synonyms:15-(S)-tert-butoxycarbonylamino-4-methoxy-12-(S)-(4-methoxybenzyl)-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.1(3,7)]-docosa-1-⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-(S)-carboxylic acid methyl ester

Chemical Property of 15-(S)-tert-butoxycarbonylamino-4-methoxy-12-(S)-(4-methoxybenzyl)-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.1(3,7)]-docosa-1-⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-(S)-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 15-(S)-tert-butoxycarbonylamino-4-methoxy-12-(S)-(4-methoxybenzyl)-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.1(3,7)]-docosa-1-⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-(S)-carboxylic acid methyl ester

There total 11 articles about 15-(S)-tert-butoxycarbonylamino-4-methoxy-12-(S)-(4-methoxybenzyl)-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.1(3,7)]-docosa-1-⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-(S)-carboxylic 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: 35.0%

2-(R)-[2-(S)-{2-(S)-tert-butoxycarbonylamino-3-[4-(5-iodo-2-methoxyphenoxy)phenyl]propionylamino}-3-(4-methoxyphenyl)-propionylamino]-3-iodopropionic acid methyl ester (327620-98-4) → 15-(S)-tert-butoxycarbonylamino-4-methoxy-12-(S)-(4-methoxybenzyl)-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.1(3,7)]-docosa-1-(20),3,5,7(22),17(21),18-hexaene-9-(S)-carboxylic acid methyl ester (192315-55-2)

Guidance literature:

2-(R)-[2-(S)-{2-(S)-tert-butoxycarbonylamino-3-[4-(5-iodo-2-methoxyphenoxy)phenyl]propionylamino}-3-(4-methoxyphenyl)-propionylamino]-3-iodopropionic acid methyl ester; With iodine; zinc; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; tris-(o-tolyl)phosphine; In tetrahydrofuran; at 60 ℃; for 16h; Further stages.;

DOI:10.1039/b008078k

Reference yield:

Boc-Tyr-OH (3978-80-1) → 15-(S)-tert-butoxycarbonylamino-4-methoxy-12-(S)-(4-methoxybenzyl)-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.1(3,7)]-docosa-1-(20),3,5,7(22),17(21),18-hexaene-9-(S)-carboxylic acid methyl ester (192315-55-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: K₂CO₃ / dimethylformamide / 96 h / 70 °C

2.1: NaHCO₃ / dimethylformamide / 16 h / 20 °C

3.1: MCPBA; NaHCO₃ / CHCl₃ / 16 h / 55 °C

4.1: K₂CO₃; MeOH

5.1: Chloramine-T hydrate; NaI / dimethylformamide / 1.5 h / 20 °C

5.2: K₂CO₃ / dimethylformamide / 16 h / 20 °C

6.1: 100 percent / aq. LiOH / tetrahydrofuran

7.1: 94 percent / EDCI; iPr₂NEt; BtOH / dimethylformamide / 16 h / 20 °C

8.1: 76 percent / (PhO)3PMeI / dimethylformamide / 0.33 h / 20 °C

9.1: Zn; I₂ / dimethylformamide / 0.5 h / 20 °C

9.2: 35 percent / Pd₂(dba)3; P(o-Tol)3 / tetrahydrofuran / 16 h / 60 °C

With methanol; lithium hydroxide; methyltriphenoxyphosphonium iodide; iodine; chloroamine-T; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; zinc; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide; 3.1: Perkin reaction;

DOI:10.1039/b008078k

Reference yield:

2-(S)-tert-butoxycarbonylamino-3-[4-(2-hydroxyphenoxy)phenyl]propionic acid methyl ester (193410-63-8) → 15-(S)-tert-butoxycarbonylamino-4-methoxy-12-(S)-(4-methoxybenzyl)-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.1(3,7)]-docosa-1-(20),3,5,7(22),17(21),18-hexaene-9-(S)-carboxylic acid methyl ester (192315-55-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Chloramine-T hydrate; NaI / dimethylformamide / 1.5 h / 20 °C

1.2: K₂CO₃ / dimethylformamide / 16 h / 20 °C

2.1: 100 percent / aq. LiOH / tetrahydrofuran

3.1: 94 percent / EDCI; iPr₂NEt; BtOH / dimethylformamide / 16 h / 20 °C

4.1: 76 percent / (PhO)3PMeI / dimethylformamide / 0.33 h / 20 °C

5.1: Zn; I₂ / dimethylformamide / 0.5 h / 20 °C

5.2: 35 percent / Pd₂(dba)3; P(o-Tol)3 / tetrahydrofuran / 16 h / 60 °C

With lithium hydroxide; methyltriphenoxyphosphonium iodide; iodine; chloroamine-T; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; sodium iodide; zinc; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1039/b008078k

upstream raw materials:

(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-3-(4-methoxy-phenyl)-propionic acid

2-(R)-[2-(S)-{2-(S)-tert-butoxycarbonylamino-3-[4-(5-iodo-2-methoxyphenoxy)phenyl]propionylamino}-3-(4-methoxyphenyl)-propionylamino]-3-iodopropionic acid methyl ester

Boc-Tyr-OH

2-(S)-tert-butoxycarbonylamino-3-[4-(2-hydroxyphenoxy)phenyl]propionic acid methyl ester

Downstream raw materials:

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

K-13