2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-3-hydroxy-propylidene)-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester

Base Information

• Chemical Name: 2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-3-hydroxy-propylidene)-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester
• CAS No.: 353520-94-2
• Molecular Formula: C₄₂H₅₁N₅O₁₁
• Molecular Weight: 801.894
• Mol file: 353520-94-2.mol

Synonyms:2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-3-hydroxy-propylidene)-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester

Chemical Property of 2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-3-hydroxy-propylidene)-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-3-hydroxy-propylidene)-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester

There total 20 articles about 2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-3-hydroxy-propylidene)-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl 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: 84.0%

2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-3-triisopropylsilanyloxy-propylidene)-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester (353520-90-8) → 2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-3-hydroxy-propylidene)-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester (353520-94-2)

Guidance literature:

With pyridine; hydrogen fluoride;

DOI:10.1002/1521-3773(20010518)40:10<1967::AID-ANIE1967>3.0.CO;2-Q DOI:10.1021/ja049821k

Reference yield:

L-Tyr-OMe (1080-06-4) → 2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-3-hydroxy-propylidene)-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester (353520-94-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / Na₂CO₃ / acetone; H₂O / 2 h / 20 °C

2: 86 percent / LiOH

3: 93 percent / I₂; Ag₂SO₄ / methanol / 1.5 h / 20 °C

4: 95 percent / [PdCl₂(dppf)]*CH₂Cl₂; KOAc / dimethylsulfoxide / 13 h / 80 °C

5: [PdCl₂(dppf)]*CH₂Cl₂; KOAc / 1,2-dimethoxy-ethane / 2 h / 80 °C

6: LiOH / tetrahydrofuran; H₂O / 1.5 h / 0 °C

7: 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride; 1-hydroxy-7-azabenzotriazole / tetrahydrofuran / 2 h / 20 °C

8: 84 percent / HF; pyridine

With pyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; hydrogen fluoride; iodine; potassium acetate; sodium carbonate; silver sulfate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; water; dimethyl sulfoxide; acetone; 4: Miyaura reaction / 5: Suzuki-Miyaura reaction;

DOI:10.1021/ja049821k

Reference yield:

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → 2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-3-hydroxy-propylidene)-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester (353520-94-2)

Guidance literature:

Multi-step reaction with 9 steps

1: thionyl chloride / 21 h / -15 - 20 °C

2: 100 percent / Na₂CO₃ / acetone; H₂O / 2 h / 20 °C

3: 86 percent / LiOH

4: 93 percent / I₂; Ag₂SO₄ / methanol / 1.5 h / 20 °C

5: 95 percent / [PdCl₂(dppf)]*CH₂Cl₂; KOAc / dimethylsulfoxide / 13 h / 80 °C

6: [PdCl₂(dppf)]*CH₂Cl₂; KOAc / 1,2-dimethoxy-ethane / 2 h / 80 °C

7: LiOH / tetrahydrofuran; H₂O / 1.5 h / 0 °C

8: 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride; 1-hydroxy-7-azabenzotriazole / tetrahydrofuran / 2 h / 20 °C

9: 84 percent / HF; pyridine

With pyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; lithium hydroxide; thionyl chloride; 1-hydroxy-7-aza-benzotriazole; hydrogen fluoride; iodine; potassium acetate; sodium carbonate; silver sulfate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; water; dimethyl sulfoxide; acetone; 5: Miyaura reaction / 6: Suzuki-Miyaura reaction;

DOI:10.1021/ja049821k

upstream raw materials:

2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-3-triisopropylsilanyloxy-propylidene)-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester

L-Tyr-OMe

L-asparagine tert-butyl ester

N-(benzyloxycarbonyl)-L-tyrosine methyl ester

Downstream raw materials:

2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester

2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester

(S)-2-((S)-3-{3-[(S)-3-((1R,2R)-2-Amino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-2-benzyloxycarbonylamino-propionylamino)-succinamic acid