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

Base Information

• Chemical Name: methyl 3(R)-[(4(S)-(4-benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetate
• CAS No.: 874163-02-7
• Molecular Formula: C₂₅H₃₄N₄O₈
• Molecular Weight: 518.567
• Mol file: 874163-02-7.mol

Synonyms:methyl 3(R)-[(4(S)-(4-benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetate

Chemical Property of methyl 3(R)-[(4(S)-(4-benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3(R)-[(4(S)-(4-benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetate

There total 5 articles about methyl 3(R)-[(4(S)-(4-benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetate 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: 61.0%

(2S,4S)-4-(((benzyloxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (874162-99-9) + 3(R)-2-oxo-1-pyrrolidineacetic acid methyl ester trifluoroacetate → methyl 3(R)-[(4(S)-(4-benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetate (874163-02-7)

Guidance literature:

With 2-chloro-1-methyl-pyridinium iodide; triethylamine; In dichloromethane; for 60h; Heating;

DOI:10.1021/jm050644n

Reference yield:

(2S,4S)-2-benzyl 1-tert-butyl 4-azidopyrrolidine-1,2-dicarboxylate (874162-96-6) → methyl 3(R)-[(4(S)-(4-benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetate (874163-02-7)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/jm050644n

Reference yield:

2-benzyl 1-(tert-butyl) (2S,4R)-4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate (865295-35-8) → methyl 3(R)-[(4(S)-(4-benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetate (874163-02-7)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/jm050644n

upstream raw materials:

(2S,4S)-4-(((benzyloxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

(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

cis-1-(1,1-dimethylethyoxycarbonyl)-4-amino-L-proline

Downstream raw materials:

3(R)-[(4(S)-((4-azido-2-hydroxy-5-iodobenzoyl)amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide

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

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

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