carbobenzoxy-D-valyl-L-proline methyl ester

Base Information

• Chemical Name: carbobenzoxy-D-valyl-L-proline methyl ester
• CAS No.: 51782-77-5
• Molecular Formula: C₁₉H₂₆N₂O₅
• Molecular Weight: 362.426
• Mol file: 51782-77-5.mol

Synonyms:carbobenzoxy-D-valyl-L-proline methyl ester

Chemical Property of carbobenzoxy-D-valyl-L-proline methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of carbobenzoxy-D-valyl-L-proline methyl ester

There total 1 articles about carbobenzoxy-D-valyl-L-proline 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:

L-proline methyl ester (2577-48-2) + carbobenzoxy-D-valine (1685-33-2) → carbobenzoxy-D-valyl-L-proline methyl ester (51782-77-5)

Guidance literature:

With dicyclohexyl-carbodiimide; In chloroform; for 20h; Ambient temperature;

DOI:10.1021/ja00365a032

Reference yield:

carbobenzoxy-D-valyl-L-proline methyl ester (51782-77-5) → O-benzyl-L-threonyl-D-valyl-L-prolylsarcosine methyl ester (79663-92-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 19.15 g / 1 N NaOH / ethanol / 20 h / Ambient temperature

2: Et₃N / acetonitrile / 0.25 h / -5 °C

3: 8.41 g / Et₃N / acetonitrile / -5 deg C, 1 h; RT, 20 h

4: H₂ / 10percent Pd/C / ethyl acetate

5: 10.7 g / Et₃N / acetonitrile / -5 deg C, 1 h, RT, 16 h

6: 1.) 4 N HCl, 2.) Rexyn 203 / 1.) dioxane, RT, 30 min, 2.) MeOH, 3 h

With hydrogenchloride; sodium hydroxide; Rexyn 203; hydrogen; triethylamine; palladium on activated charcoal; In ethanol; ethyl acetate; acetonitrile;

DOI:10.1021/ja00365a032

Reference yield:

carbobenzoxy-D-valyl-L-proline methyl ester (51782-77-5) → cyclo-(O-benzyl-L-threonyl-D-valyl-L-prolylsarcosyl-N-methyl-L-alanyl) (76805-09-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 19.15 g / 1 N NaOH / ethanol / 20 h / Ambient temperature

2: Et₃N / acetonitrile / 0.25 h / -5 °C

3: 8.41 g / Et₃N / acetonitrile / -5 deg C, 1 h; RT, 20 h

4: H₂ / 10percent Pd/C / ethyl acetate

5: 10.7 g / Et₃N / acetonitrile / -5 deg C, 1 h, RT, 16 h

6: 1.) 4 N HCl, 2.) Rexyn 203 / 1.) dioxane, RT, 30 min, 2.) MeOH, 3 h

7: 7.02 g / Et₃N / acetonitrile / -10 deg C, 1 h; RT, 16 h

8: 98 percent / 1 N NaOH / methanol / 0 deg C, 3 h; RT, 20 h

9: 4 N HCl / dioxane / 0.5 h / Ambient temperature

10: 656 mg / 1.) diisopropylethylamine, 1-hydroxybenzotriazole monohydrate, dicyclohexylcarbodiimide / CH₂Cl₂ / 120 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; Rexyn 203; hydrogen; 1-hydroxybenzotriazol-hydrate; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1021/ja00365a032

upstream raw materials:

L-proline methyl ester

carbobenzoxy-D-valine

Downstream raw materials:

carbobenzoxy-D-valyl-L-proline

carbobenzoxy-D-valyl-L-prolylsarcosine methyl ester

O-benzyl-L-threonyl-D-valyl-L-prolylsarcosine methyl ester

cyclo-(O-benzyl-L-threonyl-D-valyl-L-prolylsarcosyl-N-methyl-L-alanyl)