4-[2(R)-tert-butoxycarbonylamino-3-triphenylmethylthiopropyl]amino-2-phenylbenzoyl-(S)-methionine methyl ester

Base Information

• Chemical Name: 4-[2(R)-tert-butoxycarbonylamino-3-triphenylmethylthiopropyl]amino-2-phenylbenzoyl-(S)-methionine methyl ester
• CAS No.: 180977-20-2
• Molecular Formula: C₄₆H₅₁N₃O₅S₂
• Molecular Weight: 790.06
• DSSTox Substance ID: DTXSID701100490
• Mol file: 180977-20-2.mol

Synonyms:SCHEMBL8493199;CZJVMLLLUVKMMU-UMBAWLCISA-N;DTXSID701100490;180977-20-2;4-[2(R)-tert-butoxycarbonylamino-3-triphenylmethylthiopropyl]amino-2-phenylbenzoyl-(S)-methionine methyl ester;N-[[5-[[(2R)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-[(triphenylmethyl)thio]propyl]amino][1,1a(2)-biphenyl]-2-yl]carbonyl]-L-methionine methyl ester

Chemical Property of 4-[2(R)-tert-butoxycarbonylamino-3-triphenylmethylthiopropyl]amino-2-phenylbenzoyl-(S)-methionine methyl ester

Chemical Property:

• XLogP3: 9.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 20
• Exact Mass: 789.32701408
• Heavy Atom Count: 56
• Complexity: 1140

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CNC1=CC(=C(C=C1)C(=O)NC(CCSC)C(=O)OC)C2=CC=CC=C2)CSC(C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CNC1=CC(=C(C=C1)C(=O)N[C@@H](CCSC)C(=O)OC)C2=CC=CC=C2)CSC(C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5

Technology Process of 4-[2(R)-tert-butoxycarbonylamino-3-triphenylmethylthiopropyl]amino-2-phenylbenzoyl-(S)-methionine methyl ester

There total 6 articles about 4-[2(R)-tert-butoxycarbonylamino-3-triphenylmethylthiopropyl]amino-2-phenylbenzoyl-(S)-methionine methyl 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: 74.0%

N-α-(tert-butoxycarbonyl)-S-(triphenylmethyl)-L-cysteinal (149910-63-4) + N-(4-amino-2-phenylbenzoyl)-methionine methyl ester hydrochloride → N-[4-[N-[2(R)-(tert-butoxycarbonyl)amino-3-(triphenylmethyl)thio]propyl]amino-2-phenylbenzoyl]-methionine methyl ester (180977-20-2)

Guidance literature:

N-α-(tert-butoxycarbonyl)-S-(triphenylmethyl)-L-cysteinal; N-(4-amino-2-phenylbenzoyl)-methionine methyl ester hydrochloride; In methanol; for 0.166667h;

With sodium cyanoborohydride; In methanol; at 20 ℃; for 12h;

DOI:10.1016/S0968-0896(99)00252-7

Reference yield:

4-Nitro-2-phenyltoluene (13480-38-1) → N-[4-[N-[2(R)-(tert-butoxycarbonyl)amino-3-(triphenylmethyl)thio]propyl]amino-2-phenylbenzoyl]-methionine methyl ester (180977-20-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 85 percent / KMnO₄ / pyridine; H₂O / 5 h / Heating

2.1: 83 percent / Et₃N; EDCI; HOBT / CH₂Cl₂ / 10 h / 20 °C

3.1: SnCl₂ hydrate / ethyl acetate / 2 h / Heating

4.1: 2.97 g / aq. HCl / CH₂Cl₂; diethyl ether

5.1: methanol / 0.17 h

5.2: 74 percent / sodium cyanoborohydride / methanol / 12 h / 20 °C

With hydrogenchloride; potassium permanganate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; tin(ll) chloride; In pyridine; methanol; diethyl ether; dichloromethane; water; ethyl acetate; 1.1: Oxidation / 2.1: Acylation / 3.1: Reduction / 4.1: Addition / 5.1: Condensation / 5.2: Reduction;

DOI:10.1016/S0968-0896(99)00252-7

Reference yield:

2-bromo-4-nitrotoluene (7745-93-9) → N-[4-[N-[2(R)-(tert-butoxycarbonyl)amino-3-(triphenylmethyl)thio]propyl]amino-2-phenylbenzoyl]-methionine methyl ester (180977-20-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 88 percent / potassium carbonate hydrate; Pd(OAc)2 / acetone / 10 h / Heating

2.1: 85 percent / KMnO₄ / pyridine; H₂O / 5 h / Heating

3.1: 83 percent / Et₃N; EDCI; HOBT / CH₂Cl₂ / 10 h / 20 °C

4.1: SnCl₂ hydrate / ethyl acetate / 2 h / Heating

5.1: 2.97 g / aq. HCl / CH₂Cl₂; diethyl ether

6.1: methanol / 0.17 h

6.2: 74 percent / sodium cyanoborohydride / methanol / 12 h / 20 °C

With hydrogenchloride; palladium diacetate; potassium permanganate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; tin(ll) chloride; In pyridine; methanol; diethyl ether; dichloromethane; water; ethyl acetate; acetone; 1.1: Phenylation / 2.1: Oxidation / 3.1: Acylation / 4.1: Reduction / 5.1: Addition / 6.1: Condensation / 6.2: Reduction;

DOI:10.1016/S0968-0896(99)00252-7

upstream raw materials:

N-α-(tert-butoxycarbonyl)-S-(triphenylmethyl)-L-cysteinal

2-bromo-4-nitrotoluene

4-Nitro-2-phenyltoluene

4-amino-2-phenylbenzoylmethionine methyl ester