methyl (2S)-4-{4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(tert-butoxy)-3-oxopropyl]-1,3-benzoxazol-2-yl}-2-{[(2S)-2-[(tert-butoxycarbonyl)amino]-6-phthalimidohexanoyl]amino}butanoate

Base Information

• Chemical Name: methyl (2S)-4-{4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(tert-butoxy)-3-oxopropyl]-1,3-benzoxazol-2-yl}-2-{[(2S)-2-[(tert-butoxycarbonyl)amino]-6-phthalimidohexanoyl]amino}butanoate
• CAS No.: 443921-91-3
• Molecular Formula: C₄₆H₅₅N₅O₁₂
• Molecular Weight: 869.969

Synonyms:

Chemical Property of methyl (2S)-4-{4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(tert-butoxy)-3-oxopropyl]-1,3-benzoxazol-2-yl}-2-{[(2S)-2-[(tert-butoxycarbonyl)amino]-6-phthalimidohexanoyl]amino}butanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S)-4-{4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(tert-butoxy)-3-oxopropyl]-1,3-benzoxazol-2-yl}-2-{[(2S)-2-[(tert-butoxycarbonyl)amino]-6-phthalimidohexanoyl]amino}butanoate

There total 16 articles about methyl (2S)-4-{4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(tert-butoxy)-3-oxopropyl]-1,3-benzoxazol-2-yl}-2-{[(2S)-2-[(tert-butoxycarbonyl)amino]-6-phthalimidohexanoyl]amino}butanoate 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:

L-glutamic acid 1-methyl ester (6384-08-3) → methyl (2S)-4-{4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(tert-butoxy)-3-oxopropyl]-1,3-benzoxazol-2-yl}-2-{[(2S)-2-[(tert-butoxycarbonyl)amino]-6-phthalimidohexanoyl]amino}butanoate (443921-91-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 92 percent / NaHCO₃ / H₂O; tetrahydrofuran / 16 h / 20 °C

2.1: Et₃N; isobutyl chloroformate / CH₂Cl₂ / 0.5 h / -10 °C

2.2: CH₂Cl₂ / 16 h / -10 - 20 °C

2.3: 68 percent / propionic acid / 3 h / Heating

3.1: Me₃SiCl; Zn / dimethylformamide / 1 h / 20 °C

3.2: 67 percent / PdCl₂(PPh₃)2 / dimethylformamide / 2.25 h / 25 - 50 °C

4.1: piperidine / dimethylformamide / 1 h / 20 °C

5.1: 287 mg / N-hydroxybenzotriazole / dimethylformamide / 24 h

With piperidine; chloro-trimethyl-silane; sodium hydrogencarbonate; benzotriazol-1-ol; triethylamine; zinc; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo025615o

Reference yield:

2-amino-3-hydroxy-1-iodobenzene (443921-86-6) → methyl (2S)-4-{4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(tert-butoxy)-3-oxopropyl]-1,3-benzoxazol-2-yl}-2-{[(2S)-2-[(tert-butoxycarbonyl)amino]-6-phthalimidohexanoyl]amino}butanoate (443921-91-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Et₃N; isobutyl chloroformate / CH₂Cl₂ / 0.5 h / -10 °C

1.2: CH₂Cl₂ / 16 h / -10 - 20 °C

1.3: 68 percent / propionic acid / 3 h / Heating

2.1: Me₃SiCl; Zn / dimethylformamide / 1 h / 20 °C

2.2: 67 percent / PdCl₂(PPh₃)2 / dimethylformamide / 2.25 h / 25 - 50 °C

3.1: piperidine / dimethylformamide / 1 h / 20 °C

4.1: 287 mg / N-hydroxybenzotriazole / dimethylformamide / 24 h

With piperidine; chloro-trimethyl-silane; benzotriazol-1-ol; triethylamine; zinc; isobutyl chloroformate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo025615o

Reference yield:

2-benzyloxycarbonylamino-3-hydroxy-propionic acid tert-butyl ester (59859-77-7) → methyl (2S)-4-{4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(tert-butoxy)-3-oxopropyl]-1,3-benzoxazol-2-yl}-2-{[(2S)-2-[(tert-butoxycarbonyl)amino]-6-phthalimidohexanoyl]amino}butanoate (443921-91-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 89 percent / methyltriphenoxyphosphonium iodide / dimethylformamide / 3 h / 20 °C

2.1: Me₃SiCl; Zn / dimethylformamide / 1 h / 20 °C

2.2: 67 percent / PdCl₂(PPh₃)2 / dimethylformamide / 2.25 h / 25 - 50 °C

3.1: piperidine / dimethylformamide / 1 h / 20 °C

4.1: 287 mg / N-hydroxybenzotriazole / dimethylformamide / 24 h

With piperidine; chloro-trimethyl-silane; methyltriphenoxyphosphonium iodide; benzotriazol-1-ol; zinc; In N,N-dimethyl-formamide;

DOI:10.1021/jo025615o

upstream raw materials:

N^α-t-butoxycarbonyl-Nε-phthalimidolysine N-hydroxysuccinimide ester

L-glutamic acid 1-methyl ester

2-amino-3-hydroxy-1-iodobenzene

2-benzyloxycarbonylamino-3-hydroxy-propionic acid tert-butyl ester

Downstream raw materials:

methyl (7S,10S,13S)-10-(4-phthalimidobutyl)-7-{[(benzyloxy)carbonyl]amino}-8,11-dioxo-19-oxa-9,12,17-triazatricyclo[14.2.1.0^6,18]nonadeca-1⁽¹⁸⁾,2,4,16-tetraene-13-carboxylate

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