1,2-Pyrrolidinedicarboxylic acid, 4-(methylthio)-, 1-(1,1-dimethylethyl) ester, (2S,4R)-

Base Information

• Chemical Name: 1,2-Pyrrolidinedicarboxylic acid, 4-(methylthio)-, 1-(1,1-dimethylethyl) ester, (2S,4R)-
• CAS No.: 876953-58-1
• Molecular Formula: C11H19NO4S
• Molecular Weight: 261.33800
• Mol file: 876953-58-1.mol

Synonyms:(2S,4R)-4-Methylsulfanyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester;

Chemical Property of 1,2-Pyrrolidinedicarboxylic acid, 4-(methylthio)-, 1-(1,1-dimethylethyl) ester, (2S,4R)-

Chemical Property:

• PSA: 92.14000
• LogP: 1.74990

Purity/Quality:

99% ^*data from raw suppliers

(4R)-1-Boc-4-methylthiol-L-proline 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-Pyrrolidinedicarboxylic acid, 4-(methylthio)-, 1-(1,1-dimethylethyl) ester, (2S,4R)-

There total 6 articles about 1,2-Pyrrolidinedicarboxylic acid, 4-(methylthio)-, 1-(1,1-dimethylethyl) ester, (2S,4R)- 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: 87.0%

1-(tert-butyl) 2-methyl (2S,4R)-4-(acetylthio)pyrrolidine-1,2-dicarboxylate (188111-18-4) + dimethyl sulfate (77-78-1) → N-(tert-butyloxycarbonyl)-trans-4-(methylthio)-L-proline (876953-58-1)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 3.5h;

DOI:10.1016/j.bmc.2005.11.001

Reference yield:

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) → N-(tert-butyloxycarbonyl)-trans-4-(methylthio)-L-proline (876953-58-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 35 percent / CrO₃; pyridine / CH₂Cl₂ / 0.5 h / 0 °C

2: 97 percent / NaBH₄ / methanol; H₂O / 15 h / 4 °C

3: 63 percent / methanol; diethyl ether

4: 97 percent / Et₃N / CH₂Cl₂ / 0.33 h

5: 83 percent / dimethylformamide / 4 h / 68 °C

6: 87 percent / aq. NaOH / methanol / 3.5 h / 20 °C

With pyridine; chromium(VI) oxide; sodium hydroxide; sodium tetrahydroborate; triethylamine; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2005.11.001

Reference yield:

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester (74844-91-0,114676-69-6,135042-17-0,227935-38-8,102195-79-9) → N-(tert-butyloxycarbonyl)-trans-4-(methylthio)-L-proline (876953-58-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / Et₃N / CH₂Cl₂ / 0.33 h

2: 83 percent / dimethylformamide / 4 h / 68 °C

3: 87 percent / aq. NaOH / methanol / 3.5 h / 20 °C

With sodium hydroxide; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2005.11.001

upstream raw materials:

1-(tert-butyl) 2-methyl (2S,4R)-4-(acetylthio)pyrrolidine-1,2-dicarboxylate

dimethyl sulfate

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester

Downstream raw materials:

(2S,4R)-2-[(S)-1-((S)-1-Methoxycarbonyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-4-methylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Refernces