N-[8-(N²,N³-bis(tert-butoxycarbonyl)guanidino)octyl]-N-(1-phenethylpiperidin-4-yl)propanamide

Base Information

• Chemical Name: N-[8-(N²,N³-bis(tert-butoxycarbonyl)guanidino)octyl]-N-(1-phenethylpiperidin-4-yl)propanamide
• CAS No.: 678188-89-1
• Molecular Formula: C₃₅H₅₉N₅O₅
• Molecular Weight: 629.884

Synonyms:N-[8-(N²,N³-bis(tert-butoxycarbonyl)guanidino)octyl]-N-(1-phenethylpiperidin-4-yl)propanamide

Chemical Property of N-[8-(N²,N³-bis(tert-butoxycarbonyl)guanidino)octyl]-N-(1-phenethylpiperidin-4-yl)propanamide

Chemical Property:

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Technology Process of N-[8-(N²,N³-bis(tert-butoxycarbonyl)guanidino)octyl]-N-(1-phenethylpiperidin-4-yl)propanamide

There total 9 articles about N-[8-(N²,N³-bis(tert-butoxycarbonyl)guanidino)octyl]-N-(1-phenethylpiperidin-4-yl)propanamide 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: 95.0%

tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate (145013-05-4) + N-(8-amino-octyl)-N-(1-phenethyl-piperidin-4-yl)-propionamide (678188-85-7) → C35H59N5O5 (678188-89-1)

Guidance literature:

With triethylamine; mercury dichloride; In dichloromethane; at 20 ℃;

DOI:10.1016/j.bmcl.2003.10.048

Reference yield: 76.0%

N-(2-aminooctyl)-N-(1-phenethylpiperidin-4-yl)propionamide bis(trifluoroacetate) + tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate (145013-05-4) → N-[8-(N2,N3-bis(tert-butoxycarbonyl)guanidino)octyl]-N-(1-phenethylpiperidin-4-yl)propanamide (678188-89-1)

Guidance literature:

With triethylamine; mercury dichloride; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.bmc.2006.06.007

Reference yield:

1,8-diaminooctan (373-44-4) → N-[8-(N2,N3-bis(tert-butoxycarbonyl)guanidino)octyl]-N-(1-phenethylpiperidin-4-yl)propanamide (678188-89-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 81 percent / CHCl₃ / 0 - 20 °C

2: 82 percent / NaBH₃CN; molecular sieves 3 Angstroem; AcOH / methanol / pH 6 - 7

3: 56 percent / 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 20 °C

4: 90 percent / CH₂Cl₂ / 0.5 h / 20 °C

5: 76 percent / Et₃N; HgCl₂ / CH₂Cl₂ / 3 h / 20 °C

With pyridine; dmap; 3 A molecular sieve; sodium cyanoborohydride; acetic acid; triethylamine; mercury dichloride; In methanol; dichloromethane; chloroform;

DOI:10.1016/j.bmc.2006.06.007

upstream raw materials:

tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate

N-(8-amino-octyl)-N-(1-phenethyl-piperidin-4-yl)-propionamide

1,8-diaminooctan

tert-butyl N-(8-aminooctyl)carbamate

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