2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-2-propylcarbamoyl-ethyl)-1H-indol-7-yl]-4-methoxy-phenyl}-propionic acid

Base Information

• Chemical Name: 2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-2-propylcarbamoyl-ethyl)-1H-indol-7-yl]-4-methoxy-phenyl}-propionic acid
• CAS No.: 443764-18-9
• Molecular Formula: C₃₇H₄₄N₄O₈
• Molecular Weight: 672.778

Synonyms:2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-2-propylcarbamoyl-ethyl)-1H-indol-7-yl]-4-methoxy-phenyl}-propionic acid

Chemical Property of 2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-2-propylcarbamoyl-ethyl)-1H-indol-7-yl]-4-methoxy-phenyl}-propionic acid

Chemical Property:

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Technology Process of 2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-2-propylcarbamoyl-ethyl)-1H-indol-7-yl]-4-methoxy-phenyl}-propionic acid

There total 8 articles about 2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-2-propylcarbamoyl-ethyl)-1H-indol-7-yl]-4-methoxy-phenyl}-propionic 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: 80.0%

(S)-N-benzyloxycarbonyl-3-(4-methoxy-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl)alanine methyl ester (353520-75-9) + [2-(7-bromo-1H-indol-3-yl)-1-propylcarbamoyl-ethyl]-carbamic acid tert-butyl ester (443764-17-8) → 2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-2-propylcarbamoyl-ethyl)-1H-indol-7-yl]-4-methoxy-phenyl}-propionic acid (443764-18-9)

Guidance literature:

With potassium carbonate; [1,1'-bis(diphenylphosphino)-ferrocene]palladium(II) chloride-dichlormethane complex; In 1,2-dimethoxyethane; water; at 70 ℃;

DOI:10.1002/1521-3773(20020301)41:5<780::AID-ANIE780>3.0.CO;2-V

Reference yield:

7-bromo-1H-indole (51417-51-7) → 2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-2-propylcarbamoyl-ethyl)-1H-indol-7-yl]-4-methoxy-phenyl}-propionic acid (443764-18-9)

Guidance literature:

Multi-step reaction with 4 steps

1: tryptophane-synthetase; pyridoxal 5'-phosphate / 37 °C

2: N'-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-hydroxy-1H-benzotriazole

3: 80 percent / K₂CO₃ / [Pd(dppf)Cl₂]*CH₂Cl₂ / 1,2-dimethoxy-ethane; H₂O / 70 °C

With tryptophane-synthetase; pyridoxal 5'-phosphate; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; [1,1'-bis(diphenylphosphino)-ferrocene]palladium(II) chloride-dichlormethane complex; In 1,2-dimethoxyethane; water; 4: Suzuki cross-coupling reaction;

DOI:10.1002/1521-3773(20020301)41:5<780::AID-ANIE780>3.0.CO;2-V

Reference yield:

3-Iodo-L-tyrosine (70-78-0) → 2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-2-propylcarbamoyl-ethyl)-1H-indol-7-yl]-4-methoxy-phenyl}-propionic acid (443764-18-9)

Guidance literature:

Multi-step reaction with 5 steps

1: SOCl₂

2: K₂CO₃

3: KOCOCH₃ / PdCl₂(dppf) / CH₂Cl₂

4: 80 percent / K₂CO₃ / [Pd(dppf)Cl₂]*CH₂Cl₂ / 1,2-dimethoxy-ethane; H₂O / 70 °C

With thionyl chloride; potassium acetate; potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; [1,1'-bis(diphenylphosphino)-ferrocene]palladium(II) chloride-dichlormethane complex; In 1,2-dimethoxyethane; dichloromethane; water; 4: Miyauri-Suzuki reaction / 5: Suzuki cross-coupling reaction;

DOI:10.1002/1521-3773(20020301)41:5<780::AID-ANIE780>3.0.CO;2-V

upstream raw materials:

(S)-N-benzyloxycarbonyl-3-(4-methoxy-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl)alanine methyl ester

[2-(7-bromo-1H-indol-3-yl)-1-propylcarbamoyl-ethyl]-carbamic acid tert-butyl ester

7-bromo-1H-indole

3-Iodo-L-tyrosine

Downstream raw materials:

2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-2-propylcarbamoyl-ethyl)-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester

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