Ethyl 3-<4-Azido-6-(carboethoxy)-5-methylpyrimidin-2-yl>-3-<<2-<<(benzyloxy)carbonyl>amino>-2-carboxamidoethyl>amino>propionate

Base Information

• Chemical Name: Ethyl 3-<4-Azido-6-(carboethoxy)-5-methylpyrimidin-2-yl>-3-<<2-<<(benzyloxy)carbonyl>amino>-2-carboxamidoethyl>amino>propionate
• CAS No.: 76498-35-6
• Molecular Formula: C₂₄H₃₀N₈O₇
• Molecular Weight: 542.552
• Mol file: 76498-35-6.mol

Synonyms:

Chemical Property of Ethyl 3-<4-Azido-6-(carboethoxy)-5-methylpyrimidin-2-yl>-3-<<2-<<(benzyloxy)carbonyl>amino>-2-carboxamidoethyl>amino>propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Ethyl 3-<4-Azido-6-(carboethoxy)-5-methylpyrimidin-2-yl>-3-<<2-<<(benzyloxy)carbonyl>amino>-2-carboxamidoethyl>amino>propionate

There total 12 articles about Ethyl 3-<4-Azido-6-(carboethoxy)-5-methylpyrimidin-2-yl>-3-<<2-<<(benzyloxy)carbonyl>amino>-2-carboxamidoethyl>amino>propionate 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: 30.0%

Ethyl 3-<4-Azido-6-(carboethoxy)-5-methylpyrimidin-2-yl>-3-bromopropionate (76480-76-7) + D,L-Nα-(Carbobenzyloxy)-β-aminoalaninamide*HCl (76480-79-0) → Ethyl 3-<4-Azido-6-(carboethoxy)-5-methylpyrimidin-2-yl>-3-<<2-<<(benzyloxy)carbonyl>amino>-2-carboxamidoethyl>amino>propionate (76498-35-6)

Guidance literature:

With sodium hydrogencarbonate; In methanol; Ambient temperature;

DOI:10.1021/jo00320a037

Reference yield:

diethyl oxalpropionate (759-65-9) → Ethyl 3-<4-Azido-6-(carboethoxy)-5-methylpyrimidin-2-yl>-3-<<2-<<(benzyloxy)carbonyl>amino>-2-carboxamidoethyl>amino>propionate (76498-35-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 43 percent / KOH / ethanol / Heating

2: 65 percent / conc. HCl / H₂O

3: 67 percent / pyridine / 44 h / 85 °C

4: Ac₂O / pyridine / Ambient temperature

5: 95percent H₂SO₄ / 18 h / 70 °C

6: 92 percent / 5.5 h / Heating

7: 100 percent / H₂ / 1percent Pd/C / ethyl acetate; ethanol / 12 h / 1551.4 Torr

8: 96 percent / Phosphorous oxychloride / 0.5 h / Heating

9: 86 percent / Sodium azide / dimethylformamide / 18 h / 25 °C

10: 100 percent / Dioxane dibromide / CCl₄ / 1 h / Heating

11: 30 percent / Sodium bicarbonate / methanol / Ambient temperature

With hydrogenchloride; potassium hydroxide; sodium azide; 1,4-dioxane dibromide; sulfuric acid; hydrogen; acetic anhydride; sodium hydrogencarbonate; trichlorophosphate; palladium on activated charcoal; In pyridine; methanol; tetrachloromethane; ethanol; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00320a037

Reference yield:

2,5-Dimethyl-4-oxopyrimidine-6-carboxylic Acid (39875-10-0) → Ethyl 3-<4-Azido-6-(carboethoxy)-5-methylpyrimidin-2-yl>-3-<<2-<<(benzyloxy)carbonyl>amino>-2-carboxamidoethyl>amino>propionate (76498-35-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 67 percent / pyridine / 44 h / 85 °C

2: Ac₂O / pyridine / Ambient temperature

3: 95percent H₂SO₄ / 18 h / 70 °C

4: 92 percent / 5.5 h / Heating

5: 100 percent / H₂ / 1percent Pd/C / ethyl acetate; ethanol / 12 h / 1551.4 Torr

6: 96 percent / Phosphorous oxychloride / 0.5 h / Heating

7: 86 percent / Sodium azide / dimethylformamide / 18 h / 25 °C

8: 100 percent / Dioxane dibromide / CCl₄ / 1 h / Heating

9: 30 percent / Sodium bicarbonate / methanol / Ambient temperature

With sodium azide; 1,4-dioxane dibromide; sulfuric acid; hydrogen; acetic anhydride; sodium hydrogencarbonate; trichlorophosphate; palladium on activated charcoal; In pyridine; methanol; tetrachloromethane; ethanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00320a037

upstream raw materials:

Ethyl 3-<4-Azido-6-(carboethoxy)-5-methylpyrimidin-2-yl>-3-bromopropionate

D,L-N^α-(Carbobenzyloxy)-β-aminoalaninamide*HCl

diethyl oxalpropionate

N^α-(Carbobenzyloxy)-β-chloroalanine methyl ester