(S)-1-[(S)-2-((R)-2,6-Dioxo-1,7-diaza-spiro[4.4]non-8-en-7-yl)-3-phenyl-propionyl]-pyrrolidine-2-carboxylic acid amide

Base Information

• Chemical Name: (S)-1-[(S)-2-((R)-2,6-Dioxo-1,7-diaza-spiro[4.4]non-8-en-7-yl)-3-phenyl-propionyl]-pyrrolidine-2-carboxylic acid amide
• CAS No.: 406479-02-5
• Molecular Formula: C₂₁H₂₄N₄O₄
• Molecular Weight: 396.446

Synonyms:(S)-1-[(S)-2-((R)-2,6-Dioxo-1,7-diaza-spiro[4.4]non-8-en-7-yl)-3-phenyl-propionyl]-pyrrolidine-2-carboxylic acid amide

Chemical Property of (S)-1-[(S)-2-((R)-2,6-Dioxo-1,7-diaza-spiro[4.4]non-8-en-7-yl)-3-phenyl-propionyl]-pyrrolidine-2-carboxylic acid amide

Chemical Property:

Purity/Quality:

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Technology Process of (S)-1-[(S)-2-((R)-2,6-Dioxo-1,7-diaza-spiro[4.4]non-8-en-7-yl)-3-phenyl-propionyl]-pyrrolidine-2-carboxylic acid amide

There total 8 articles about (S)-1-[(S)-2-((R)-2,6-Dioxo-1,7-diaza-spiro[4.4]non-8-en-7-yl)-3-phenyl-propionyl]-pyrrolidine-2-carboxylic acid amide 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: 58.0%

Nα-[(5R,8RS)-8-tert-butyldimethylsilyloxy-2,6-dioxo-1-azaspiro[4.4]octyl]-L-phenylalanyl-L-prolinamide (406479-01-4) → (S)-1-[(S)-2-((R)-2,6-Dioxo-1,7-diaza-spiro[4.4]non-8-en-7-yl)-3-phenyl-propionyl]-pyrrolidine-2-carboxylic acid amide (406479-02-5)

Guidance literature:

With silica gel; In dichloromethane; at 25 - 200 ℃; for 1.25h; under 30 - 40 Torr;

DOI:10.1016/S0968-0896(01)00287-5

Reference yield:

L-phenylalanine benzyl ester hydrochloride (2462-32-0) → (S)-1-[(S)-2-((R)-2,6-Dioxo-1,7-diaza-spiro[4.4]non-8-en-7-yl)-3-phenyl-propionyl]-pyrrolidine-2-carboxylic acid amide (406479-02-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: HOBt; NEM; EDC / CH₂Cl₂ / 0.08 h / 0 °C

1.2: 100 percent / CH₂Cl₂ / 2 h / 25 °C

2.1: OsO₄ / tetrahydrofuran; H₂O / 0.08 h / 25 °C

2.2: 100 percent / NaIO₄ / tetrahydrofuran; H₂O / 5 h / 25 °C

3.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 25 °C

4.1: 97 percent Spectr_. / H₂ / 5 percent Pd/C / CH₂Cl₂ / 18 h / 25 °C

5.1: HOBt; Et₃N; EDC / CH₂Cl₂ / 0.08 h / 0 °C

5.2: 0.406 g / CH₂Cl₂ / 2.5 h / 0 - 25 °C

6.1: 58 percent / SiO₂ / CH₂Cl₂ / 1.25 h / 25 - 200 °C / 30 - 40 Torr

With 2,6-dimethylpyridine; N-Ethylmaleimide; osmium(VIII) oxide; hydrogen; silica gel; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/S0968-0896(01)00287-5

Reference yield:

(R)-2-allyl-5-oxopyrrolidine-2-carboxylic acid (406478-96-4) → (S)-1-[(S)-2-((R)-2,6-Dioxo-1,7-diaza-spiro[4.4]non-8-en-7-yl)-3-phenyl-propionyl]-pyrrolidine-2-carboxylic acid amide (406479-02-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: HOBt; NEM; EDC / CH₂Cl₂ / 0.08 h / 0 °C

1.2: 100 percent / CH₂Cl₂ / 2 h / 25 °C

2.1: OsO₄ / tetrahydrofuran; H₂O / 0.08 h / 25 °C

2.2: 100 percent / NaIO₄ / tetrahydrofuran; H₂O / 5 h / 25 °C

3.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 25 °C

4.1: 97 percent Spectr_. / H₂ / 5 percent Pd/C / CH₂Cl₂ / 18 h / 25 °C

5.1: HOBt; Et₃N; EDC / CH₂Cl₂ / 0.08 h / 0 °C

5.2: 0.406 g / CH₂Cl₂ / 2.5 h / 0 - 25 °C

6.1: 58 percent / SiO₂ / CH₂Cl₂ / 1.25 h / 25 - 200 °C / 30 - 40 Torr

With 2,6-dimethylpyridine; N-Ethylmaleimide; osmium(VIII) oxide; hydrogen; silica gel; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/S0968-0896(01)00287-5

upstream raw materials:

N^α-[(5R,8RS)-8-tert-butyldimethylsilyloxy-2,6-dioxo-1-azaspiro[4.4]octyl]-L-phenylalanyl-L-prolinamide

L-phenylalanine benzyl ester hydrochloride

(R)-2-allyl-5-oxopyrrolidine-2-carboxylic acid

N^α-[(5R,8RS)-8-hydroxy-2,6-dioxo-1-azaspiro[4.4]octyl]-L-phenylalanine benzyl ester

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