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

Base Information

• Chemical Name: [(1-{2-[(2S,3R)-3-Benzyloxy-2-((S)-2-methylamino-propionylamino)-butyrylamino]-3-methyl-butyryl}-pyrrolidine-2-carbonyl)-methyl-amino]-acetic acid; hydrochloride
• CAS No.: 80534-20-9
• Molecular Formula: C₂₈H₄₃N₅O₇*ClH
• Molecular Weight: 598.14

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about [(1-{2-[(2S,3R)-3-Benzyloxy-2-((S)-2-methylamino-propionylamino)-butyrylamino]-3-methyl-butyryl}-pyrrolidine-2-carbonyl)-methyl-amino]-acetic acid; hydrochloride 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) → [(1-{2-[(2S,3R)-3-Benzyloxy-2-((S)-2-methylamino-propionylamino)-butyrylamino]-3-methyl-butyryl}-pyrrolidine-2-carbonyl)-methyl-amino]-acetic acid; hydrochloride (80534-20-9)

Guidance literature:

Multi-step reaction with 10 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

9: 98 percent / 1 N NaOH / methanol / 0 deg C, 3 h; RT, 20 h

10: 4 N HCl / dioxane / 0.5 h / Ambient temperature

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

DOI:10.1021/ja00365a032

Reference yield:

carbobenzoxy-D-valine (1685-33-2) → [(1-{2-[(2S,3R)-3-Benzyloxy-2-((S)-2-methylamino-propionylamino)-butyrylamino]-3-methyl-butyryl}-pyrrolidine-2-carbonyl)-methyl-amino]-acetic acid; hydrochloride (80534-20-9)

Guidance literature:

Multi-step reaction with 10 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

9: 98 percent / 1 N NaOH / methanol / 0 deg C, 3 h; RT, 20 h

10: 4 N HCl / dioxane / 0.5 h / Ambient temperature

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

DOI:10.1021/ja00365a032

Reference yield:

carbobenzoxy-D-valyl-L-proline methyl ester (51782-77-5) → [(1-{2-[(2S,3R)-3-Benzyloxy-2-((S)-2-methylamino-propionylamino)-butyrylamino]-3-methyl-butyryl}-pyrrolidine-2-carbonyl)-methyl-amino]-acetic acid; hydrochloride (80534-20-9)

Guidance literature:

Multi-step reaction with 9 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

With hydrogenchloride; sodium hydroxide; Rexyn 203; hydrogen; triethylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; ethyl acetate; acetonitrile;

DOI:10.1021/ja00365a032

upstream raw materials:

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

N-Boc-O-benzyl-L-threonine

L-proline methyl ester

C₂₁H₃₁NO₇

Downstream raw materials:

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

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