(3S)-3-[[(2S)-2-amino-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]amino]hexanoyl]amino]-4-[[(2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]-[(2S)-2-(methylamino)-3-phenylpropanoyl]amino]-4-oxobutanoic acid

Base Information

• Chemical Name: (3S)-3-[[(2S)-2-amino-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]amino]hexanoyl]amino]-4-[[(2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]-[(2S)-2-(methylamino)-3-phenylpropanoyl]amino]-4-oxobutanoic acid
• CAS No.: 131449-37-1
• Molecular Formula: C₄₅H₅₅N₇O₁₀
• Molecular Weight: 853.973
• Mol file: 131449-37-1.mol

Synonyms:A 70874;A-70874;Boc-Trp-Lys(epsilon-N-4-hydroxycinnamoyl)-Asp-(N-methyl)Phe-NH2

Chemical Property of (3S)-3-[[(2S)-2-amino-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]amino]hexanoyl]amino]-4-[[(2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]-[(2S)-2-(methylamino)-3-phenylpropanoyl]amino]-4-oxobutanoic acid

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.299g/cm³
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 22
• Exact Mass: 853.40104098
• Heavy Atom Count: 62
• Complexity: 1560

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)N(C(=O)C(CC3=CC=CC=C3)NC)C(=O)C(CC(=O)O)NC(=O)C(CCCCNC(=O)C=CC4=CC=C(C=C4)O)N
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N(C(=O)[C@H](CC3=CC=CC=C3)NC)C(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCCCNC(=O)/C=C/C4=CC=C(C=C4)O)N

Technology Process of (3S)-3-[[(2S)-2-amino-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]amino]hexanoyl]amino]-4-[[(2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]-[(2S)-2-(methylamino)-3-phenylpropanoyl]amino]-4-oxobutanoic acid

There total 5 articles about (3S)-3-[[(2S)-2-amino-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]amino]hexanoyl]amino]-4-[[(2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]-[(2S)-2-(methylamino)-3-phenylpropanoyl]amino]-4-oxobutanoic 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:

Boc-Trp-OH (13139-14-5) → Boc-Trp-Lysε-(4-hydroxycinnamoyl)>-Asp-(NMe)Phe-NH2 (131449-37-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / 1-hydroxybenzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂; dimethylformamide / 20 h / Ambient temperature

2: 78 percent / H₂, glacial acetic acid / 10percent Pd-C / 3 h / 760 Torr

3: N-methylmorpholine / dimethylformamide / from 0 deg C to RT, overnight

With 4-methyl-morpholine; hydrogen; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00089a010

Reference yield:

Boc-Trp-Lys(Cbz)-Asp(OBzl)-(NMe)Phe-NH2 (131450-75-4) → Boc-Trp-Lysε-(4-hydroxycinnamoyl)>-Asp-(NMe)Phe-NH2 (131449-37-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / H₂, glacial acetic acid / 10percent Pd-C / 3 h / 760 Torr

2: N-methylmorpholine / dimethylformamide / from 0 deg C to RT, overnight

With 4-methyl-morpholine; hydrogen; acetic acid; palladium on activated charcoal; In N,N-dimethyl-formamide;

DOI:10.1021/jm00089a010

Reference yield:

Boc-Lys(Cbz)-Asp(OBzl)-(NMe)Phe-NH2 hydrochloride → Boc-Trp-Lysε-(4-hydroxycinnamoyl)>-Asp-(NMe)Phe-NH2 (131449-37-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / 1-hydroxybenzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂; dimethylformamide / 20 h / Ambient temperature

2: 78 percent / H₂, glacial acetic acid / 10percent Pd-C / 3 h / 760 Torr

3: N-methylmorpholine / dimethylformamide / from 0 deg C to RT, overnight

With 4-methyl-morpholine; hydrogen; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00089a010

upstream raw materials:

4-hydroxycinnamic acid N-hydroxysuccinimide ester

Boc-Trp-Lys-Asp-(NMe)Phe-NH₂

p-Coumaric Acid

Boc-Trp-OH

Refernces