methyl 4-(N-acetylamino)-5-[N',N-di(tert-butoxycarbonyl)guanidino]-3-(2-pentyloxy)benzoate

Base Information

• Chemical Name: methyl 4-(N-acetylamino)-5-[N',N-di(tert-butoxycarbonyl)guanidino]-3-(2-pentyloxy)benzoate
• CAS No.: 257292-17-4
• Molecular Formula: C₂₆H₄₀N₄O₈
• Molecular Weight: 536.626
• Mol file: 257292-17-4.mol

Synonyms:methyl 4-(N-acetylamino)-5-[N',N-di(tert-butoxycarbonyl)guanidino]-3-(2-pentyloxy)benzoate

Chemical Property of methyl 4-(N-acetylamino)-5-[N',N-di(tert-butoxycarbonyl)guanidino]-3-(2-pentyloxy)benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-(N-acetylamino)-5-[N',N-di(tert-butoxycarbonyl)guanidino]-3-(2-pentyloxy)benzoate

There total 6 articles about methyl 4-(N-acetylamino)-5-[N',N-di(tert-butoxycarbonyl)guanidino]-3-(2-pentyloxy)benzoate 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: 92.0%

1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea (107819-90-9) + methyl 4-(N-acetylamino)-5-amino-3-(2-pentyloxy)benzoate (257292-16-3) → methyl 4-(N-acetylamino)-5-[N',N-di(tert-butoxycarbonyl)guanidino]-3-(2-pentyloxy)benzoate (257292-17-4)

Guidance literature:

With triethylamine; mercury dichloride; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1016/S0968-0896(99)00197-2

Reference yield:

4-aminosalicylic acid (2374-03-0) → methyl 4-(N-acetylamino)-5-[N',N-di(tert-butoxycarbonyl)guanidino]-3-(2-pentyloxy)benzoate (257292-17-4)

Guidance literature:

Multi-step reaction with 7 steps

1: conc. H₂SO₄ / 14 h / Heating

2: 100 percent / DMAP / 12 h / 20 °C

3: 42.7 percent / HNO₃; Ac₂O / dioxane / 5 h / 20 °C

4: 89.7 percent / Zn; MeOH / 1.5 h / 20 °C

5: 82 percent / K₂CO₃ / acetone / 14 h / Heating

6: 99 percent / H₂ / Pd/C / methanol / 1 h / 1551.44 Torr

7: 92 percent / Et₃N; HgCl₂ / dimethylformamide / 0 - 20 °C

With methanol; dmap; sulfuric acid; hydrogen; nitric acid; acetic anhydride; potassium carbonate; triethylamine; mercury dichloride; zinc; palladium on activated charcoal; In 1,4-dioxane; methanol; N,N-dimethyl-formamide; acetone; 1: Esterification / 2: Acetylation / 3: Nitration / 4: Substitution / 5: Alkylation / 6: Catalytic hydrogenation / 7: Substitution;

DOI:10.1016/S0968-0896(99)00197-2

Reference yield:

methyl 4-(N-acetylamino)-3-acetyloxybenzoate (205527-84-0) → methyl 4-(N-acetylamino)-5-[N',N-di(tert-butoxycarbonyl)guanidino]-3-(2-pentyloxy)benzoate (257292-17-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 42.7 percent / HNO₃; Ac₂O / dioxane / 5 h / 20 °C

2: 89.7 percent / Zn; MeOH / 1.5 h / 20 °C

3: 82 percent / K₂CO₃ / acetone / 14 h / Heating

4: 99 percent / H₂ / Pd/C / methanol / 1 h / 1551.44 Torr

5: 92 percent / Et₃N; HgCl₂ / dimethylformamide / 0 - 20 °C

With methanol; hydrogen; nitric acid; acetic anhydride; potassium carbonate; triethylamine; mercury dichloride; zinc; palladium on activated charcoal; In 1,4-dioxane; methanol; N,N-dimethyl-formamide; acetone; 1: Nitration / 2: Substitution / 3: Alkylation / 4: Catalytic hydrogenation / 5: Substitution;

DOI:10.1016/S0968-0896(99)00197-2

upstream raw materials:

1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea

methyl 4-(N-acetylamino)-5-amino-3-(2-pentyloxy)benzoate

4-aminosalicylic acid

methyl 4-(N-acetylamino)-3-acetyloxybenzoate