N-tert-butoxycarbonyl-N-methyl-L-alanyl-O-benzyl-L-threonyl-D-valyl-L-prolylsarcosine methyl ester

Base Information

• Chemical Name: N-tert-butoxycarbonyl-N-methyl-L-alanyl-O-benzyl-L-threonyl-D-valyl-L-prolylsarcosine methyl ester
• CAS No.: 79663-90-4
• Molecular Formula: C₃₄H₅₃N₅O₉
• Molecular Weight: 675.823
• Mol file: 79663-90-4.mol

Synonyms:N-tert-butoxycarbonyl-N-methyl-L-alanyl-O-benzyl-L-threonyl-D-valyl-L-prolylsarcosine methyl ester

Chemical Property of N-tert-butoxycarbonyl-N-methyl-L-alanyl-O-benzyl-L-threonyl-D-valyl-L-prolylsarcosine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-tert-butoxycarbonyl-N-methyl-L-alanyl-O-benzyl-L-threonyl-D-valyl-L-prolylsarcosine methyl ester

There total 12 articles about N-tert-butoxycarbonyl-N-methyl-L-alanyl-O-benzyl-L-threonyl-D-valyl-L-prolylsarcosine 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) → N-tert-butoxycarbonyl-N-methyl-L-alanyl-O-benzyl-L-threonyl-D-valyl-L-prolylsarcosine methyl ester (79663-90-4)

Guidance literature:

Multi-step reaction with 8 steps

1: dicyclohexylcarbodiimide / CHCl₃ / 20 h / Ambient temperature

2: 19.15 g / 1 N NaOH / ethanol / 20 h / Ambient temperature

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

4: 8.41 g / Et₃N / acetonitrile / -5 deg C, 1 h; RT, 20 h

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

6: 10.7 g / Et₃N / acetonitrile / -5 deg C, 1 h, RT, 16 h

7: 1.) 4 N HCl, 2.) Rexyn 203 / 1.) dioxane, RT, 30 min, 2.) MeOH, 3 h

8: 7.02 g / Et₃N / acetonitrile / -10 deg C, 1 h; RT, 16 h

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

DOI:10.1021/ja00365a032

Reference yield:

carbobenzoxy-D-valine (1685-33-2) → N-tert-butoxycarbonyl-N-methyl-L-alanyl-O-benzyl-L-threonyl-D-valyl-L-prolylsarcosine methyl ester (79663-90-4)

Guidance literature:

Multi-step reaction with 8 steps

1: dicyclohexylcarbodiimide / CHCl₃ / 20 h / Ambient temperature

2: 19.15 g / 1 N NaOH / ethanol / 20 h / Ambient temperature

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

4: 8.41 g / Et₃N / acetonitrile / -5 deg C, 1 h; RT, 20 h

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

6: 10.7 g / Et₃N / acetonitrile / -5 deg C, 1 h, RT, 16 h

7: 1.) 4 N HCl, 2.) Rexyn 203 / 1.) dioxane, RT, 30 min, 2.) MeOH, 3 h

8: 7.02 g / Et₃N / acetonitrile / -10 deg C, 1 h; RT, 16 h

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

DOI:10.1021/ja00365a032

Reference yield:

carbobenzoxy-D-valyl-L-proline methyl ester (51782-77-5) → N-tert-butoxycarbonyl-N-methyl-L-alanyl-O-benzyl-L-threonyl-D-valyl-L-prolylsarcosine methyl ester (79663-90-4)

Guidance literature:

Multi-step reaction with 7 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

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

DOI:10.1021/ja00365a032

upstream raw materials:

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

N-Boc-O-benzyl-L-threonine

N-(tert-butoxycarbonyl)-N-methyl-L-alanine

L-proline methyl ester

Downstream raw materials:

N-tert-butoxycarbonyl-N-methyl-L-alanyl-O-benzyl-L-threonyl-D-valyl-L-prolylsarcosine

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

[(1-{2-[(2S,3R)-3-Benzyloxy-2-((S)-2-methylamino-propionylamino)-butyrylamino]-3-methyl-butyryl}-pyrrolidine-2-carbonyl)-methyl-amino]-acetic acid; hydrochloride