1-Pyrrolidinecarboxylic acid, 2-[[[(3R)-1-(2-amino-2-oxoethyl)-2-oxo-3-pyrrolidinyl]amino]carbonyl]-4-[ (4-azido-2-hydroxybenzoyl)amino]-, 1,1-dimethylethyl ester, (2S,4S)-

Base Information

• Chemical Name: 1-Pyrrolidinecarboxylic acid, 2-[[[(3R)-1-(2-amino-2-oxoethyl)-2-oxo-3-pyrrolidinyl]amino]carbonyl]-4-[ (4-azido-2-hydroxybenzoyl)amino]-, 1,1-dimethylethyl ester, (2S,4S)-
• CAS No.: 874163-07-2
• Molecular Formula: C23H30N8O7
• Molecular Weight: 530.541
• Mol file: 874163-07-2.mol

Synonyms:

Chemical Property of 1-Pyrrolidinecarboxylic acid, 2-[[[(3R)-1-(2-amino-2-oxoethyl)-2-oxo-3-pyrrolidinyl]amino]carbonyl]-4-[ (4-azido-2-hydroxybenzoyl)amino]-, 1,1-dimethylethyl ester, (2S,4S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Pyrrolidinecarboxylic acid, 2-[[[(3R)-1-(2-amino-2-oxoethyl)-2-oxo-3-pyrrolidinyl]amino]carbonyl]-4-[ (4-azido-2-hydroxybenzoyl)amino]-, 1,1-dimethylethyl ester, (2S,4S)-

There total 9 articles about 1-Pyrrolidinecarboxylic acid, 2-[[[(3R)-1-(2-amino-2-oxoethyl)-2-oxo-3-pyrrolidinyl]amino]carbonyl]-4-[ (4-azido-2-hydroxybenzoyl)amino]-, 1,1-dimethylethyl ester, (2S,4S)- 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: 51.0%

3(R)-[(4(S)-(4-amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide (877262-55-0) + succinimide 4-azidosalicylate (96602-46-9) → 3(R)-[(4(S)-((4-azido-2-hydroxybenzoyl)amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide (874163-07-2)

Guidance literature:

In acetonitrile; for 18h; Heating;

DOI:10.1021/jm050644n

Reference yield:

(2S,4S)-2-benzyl 1-tert-butyl 4-azidopyrrolidine-1,2-dicarboxylate (874162-96-6) → 3(R)-[(4(S)-((4-azido-2-hydroxybenzoyl)amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide (874163-07-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / H₂ / Pd/C / ethanol; H₂O / 28 h / 3878.61 Torr

2: 80 percent / aq. NaOH / 0 - 20 °C

3: 61 percent / Et₃N; 2-chloro-1-methylpyridinium iodide / CH₂Cl₂ / 60 h / Heating

4: 88 percent / NH₃ / methanol / 20 h / 20 °C

5: H₂ / Pd/C / methanol / 24 h / 2585.74 Torr

6: 51 percent / acetonitrile / 18 h / Heating

With sodium hydroxide; 2-chloro-1-methyl-pyridinium iodide; ammonia; hydrogen; triethylamine; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; acetonitrile;

DOI:10.1021/jm050644n

Reference yield:

2-benzyl 1-(tert-butyl) (2S,4R)-4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate (865295-35-8) → 3(R)-[(4(S)-((4-azido-2-hydroxybenzoyl)amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide (874163-07-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 96 percent / NaN₃ / dimethylformamide / 18.5 h / 55 °C

2: 91 percent / H₂ / Pd/C / ethanol; H₂O / 28 h / 3878.61 Torr

3: 80 percent / aq. NaOH / 0 - 20 °C

4: 61 percent / Et₃N; 2-chloro-1-methylpyridinium iodide / CH₂Cl₂ / 60 h / Heating

5: 88 percent / NH₃ / methanol / 20 h / 20 °C

6: H₂ / Pd/C / methanol / 24 h / 2585.74 Torr

7: 51 percent / acetonitrile / 18 h / Heating

With sodium hydroxide; sodium azide; 2-chloro-1-methyl-pyridinium iodide; ammonia; hydrogen; triethylamine; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm050644n

upstream raw materials:

3(R)-[(4(S)-(4-amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide

succinimide 4-azidosalicylate

(2S,4S)-2-benzyl 1-tert-butyl 4-azidopyrrolidine-1,2-dicarboxylate

2-benzyl 1-(tert-butyl) (2S,4R)-4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate