tert-butyl (S)-5-(3-(4-methoxy-2,3,6-trimethylphenylsulfonyl)guanidino)-1-oxo-1-(thiazol-2-yl)pentan-2-ylcarbamate

Base Information

• Chemical Name: tert-butyl (S)-5-(3-(4-methoxy-2,3,6-trimethylphenylsulfonyl)guanidino)-1-oxo-1-(thiazol-2-yl)pentan-2-ylcarbamate
• CAS No.: 201006-25-9
• Molecular Formula: C₂₄H₃₅N₅O₆S₂
• Molecular Weight: 553.704

Synonyms:tert-butyl (S)-5-(3-(4-methoxy-2,3,6-trimethylphenylsulfonyl)guanidino)-1-oxo-1-(thiazol-2-yl)pentan-2-ylcarbamate

Chemical Property of tert-butyl (S)-5-(3-(4-methoxy-2,3,6-trimethylphenylsulfonyl)guanidino)-1-oxo-1-(thiazol-2-yl)pentan-2-ylcarbamate

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Technology Process of tert-butyl (S)-5-(3-(4-methoxy-2,3,6-trimethylphenylsulfonyl)guanidino)-1-oxo-1-(thiazol-2-yl)pentan-2-ylcarbamate

There total 2 articles about tert-butyl (S)-5-(3-(4-methoxy-2,3,6-trimethylphenylsulfonyl)guanidino)-1-oxo-1-(thiazol-2-yl)pentan-2-ylcarbamate 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:

Nα-(t-butyloxycarbonyl)-Nω-(4-methoxy-2,3,6-trimethylbenzenesulphonyl)-L-arginine (102185-38-6,200122-49-2) → tert-butyl (S)-5-(3-(4-methoxy-2,3,6-trimethylphenylsulfonyl)guanidino)-1-oxo-1-(thiazol-2-yl)pentan-2-ylcarbamate (201006-25-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 92 percent / 1-hydroxybenzotriazole; N,N-diisopropylethylamine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / tetrahydrofuran / 4.5 h / 20 °C

2.1: TMEDA; nBuLi / tetrahydrofuran; hexane / 0.42 h / -50 - -41 °C

2.2: 75 percent / tetrahydrofuran; hexane / 0.75 h / -78 °C

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane;

DOI:10.1021/jm060978s

Reference yield:

→ tert-butyl (S)-5-(3-(4-methoxy-2,3,6-trimethylphenylsulfonyl)guanidino)-1-oxo-1-(thiazol-2-yl)pentan-2-ylcarbamate (201006-25-9)

Guidance literature:

Reference yield:

tert-butyl (S)-5-(3-(4-methoxy-2,3,6-trimethylphenylsulfonyl)guanidino)-1-oxo-1-(thiazol-2-yl)pentan-2-ylcarbamate (201006-25-9) → (S)-N-[[[4-amino-5-oxo-5-(2-thiazolyl)pentyl]amino]iminomethyl]-4-methoxy-2,3,6-trimethyl-benzenesulfonamide (201541-51-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃;

DOI:10.1016/j.bmcl.2006.02.052

upstream raw materials:

Nα-(t-butyloxycarbonyl)-Nω-(4-methoxy-2,3,6-trimethylbenzenesulphonyl)-L-arginine

Downstream raw materials:

(S)-N-[[[4-amino-5-oxo-5-(2-thiazolyl)pentyl]amino]iminomethyl]-4-methoxy-2,3,6-trimethyl-benzenesulfonamide

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