[(S)-1-[(R)-1-({[(S)-2-((S)-2-Carbamoyl-pyrrolidin-1-yl)-1-(4-nitro-benzyl)-2-oxo-ethylcarbamoyl]-methyl}-carbamoyl)-4-guanidino-butylcarbamoyl]-2-(4-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(S)-1-[(R)-1-({[(S)-2-((S)-2-Carbamoyl-pyrrolidin-1-yl)-1-(4-nitro-benzyl)-2-oxo-ethylcarbamoyl]-methyl}-carbamoyl)-4-guanidino-butylcarbamoyl]-2-(4-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester
• CAS No.: 88331-12-8
• Molecular Formula: C₃₆H₅₀N₁₀O₁₀
• Molecular Weight: 782.854
• Mol file: 88331-12-8.mol

Synonyms:[(S)-1-[(R)-1-({[(S)-2-((S)-2-Carbamoyl-pyrrolidin-1-yl)-1-(4-nitro-benzyl)-2-oxo-ethylcarbamoyl]-methyl}-carbamoyl)-4-guanidino-butylcarbamoyl]-2-(4-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester

Chemical Property of [(S)-1-[(R)-1-({[(S)-2-((S)-2-Carbamoyl-pyrrolidin-1-yl)-1-(4-nitro-benzyl)-2-oxo-ethylcarbamoyl]-methyl}-carbamoyl)-4-guanidino-butylcarbamoyl]-2-(4-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(S)-1-[(R)-1-({[(S)-2-((S)-2-Carbamoyl-pyrrolidin-1-yl)-1-(4-nitro-benzyl)-2-oxo-ethylcarbamoyl]-methyl}-carbamoyl)-4-guanidino-butylcarbamoyl]-2-(4-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester

There total 8 articles about [(S)-1-[(R)-1-({[(S)-2-((S)-2-Carbamoyl-pyrrolidin-1-yl)-1-(4-nitro-benzyl)-2-oxo-ethylcarbamoyl]-methyl}-carbamoyl)-4-guanidino-butylcarbamoyl]-2-(4-hydroxy-phenyl)-ethyl]-carbamic 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:

Boc-Tyr-OH (3978-80-1) → [(S)-1-[(R)-1-({[(S)-2-((S)-2-Carbamoyl-pyrrolidin-1-yl)-1-(4-nitro-benzyl)-2-oxo-ethylcarbamoyl]-methyl}-carbamoyl)-4-guanidino-butylcarbamoyl]-2-(4-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester (88331-12-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NMM, isobutyl chloroformate, 2.) NMM / 1.) THF, -15 deg C, 2.5 min, 2.) DMF, H₂O, -15 deg C, 2.5 h

2: 77 percent / NaOH / methanol; H₂O / 1 h / 23 °C

3: 1.) HOBT, DCCI, 2.) NMM / 1.) DMF, -5 deg C, 30 min, 2.) 4 deg C, 72 h

With 4-methyl-morpholine; sodium hydroxide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; isobutyl chloroformate; In methanol; water;

DOI:10.1021/jm00400a012

Reference yield:

Boc-Phe(p-NO2)-OH (33305-77-0) → [(S)-1-[(R)-1-({[(S)-2-((S)-2-Carbamoyl-pyrrolidin-1-yl)-1-(4-nitro-benzyl)-2-oxo-ethylcarbamoyl]-methyl}-carbamoyl)-4-guanidino-butylcarbamoyl]-2-(4-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester (88331-12-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) HOBT, DCCI, 2.) NMM / 1.) DMF, -5 deg C, 30 min, 2.) 4 deg C, 18 h

2: 106 percent / HCl gas / ethanol; ethyl acetate / 1 h / 15 - 20 °C

3: 1.) NMM, isobutyl chloroformate, 2.) NMM / 1.) THF, -15 deg C, 2.5 min, 2.) DMF, H₂O, -15 deg C, 2.5 h

4: 89 percent / HCl / acetic acid / 0.75 h / Ambient temperature

5: 1.) HOBT, DCCI, 2.) NMM / 1.) DMF, -5 deg C, 30 min, 2.) 4 deg C, 72 h

With 4-methyl-morpholine; hydrogenchloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; isobutyl chloroformate; In ethanol; acetic acid; ethyl acetate;

DOI:10.1021/jm00400a012

Reference yield:

methyl (2R)-2-amino-5-carbamimidamidopentanoate dihydrochloride (22888-59-1,26340-89-6,78851-84-0,111237-99-1,18598-71-5) → [(S)-1-[(R)-1-({[(S)-2-((S)-2-Carbamoyl-pyrrolidin-1-yl)-1-(4-nitro-benzyl)-2-oxo-ethylcarbamoyl]-methyl}-carbamoyl)-4-guanidino-butylcarbamoyl]-2-(4-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester (88331-12-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NMM, isobutyl chloroformate, 2.) NMM / 1.) THF, -15 deg C, 2.5 min, 2.) DMF, H₂O, -15 deg C, 2.5 h

2: 77 percent / NaOH / methanol; H₂O / 1 h / 23 °C

3: 1.) HOBT, DCCI, 2.) NMM / 1.) DMF, -5 deg C, 30 min, 2.) 4 deg C, 72 h

With 4-methyl-morpholine; sodium hydroxide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; isobutyl chloroformate; In methanol; water;

DOI:10.1021/jm00400a012

upstream raw materials:

N-(tert-butyloxycarbonyl)-L-tyrosyl-D-arginine hydrochloride

glycyl-L-4-nitrophenylalanyl-L-prolinamide hydrochloride

Boc-Tyr-OH

Boc-Phe(p-NO₂)-OH

Downstream raw materials:

N¹-amidino-L-tyrosyl-D-arginylglycyl-L-4-nitrophenylalanyl-L-prolinamide diacetate

L-tyrosyl-D-arginylglycyl-L-4-nitrophenylalanyl-L-prolinamide diacetate