Proline, 5-thioxo-, ethyl ester (9CI)

Base Information

• Chemical Name: Proline, 5-thioxo-, ethyl ester (9CI)
• CAS No.: 84911-17-1
• Molecular Formula: C7H11 N O2 S
• Molecular Weight: 173.23274
• Mol file: 84911-17-1.mol

Synonyms:DL-Proline,5-thioxo-, ethyl ester

Chemical Property of Proline, 5-thioxo-, ethyl ester (9CI)

Chemical Property:

• PSA: 70.42000
• LogP: 0.95770

Purity/Quality:

97% ^*data from raw suppliers

Ethyl5-Thioxopyrrolidine-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Proline, 5-thioxo-, ethyl ester (9CI)

There total 1 articles about Proline, 5-thioxo-, ethyl ester (9CI) 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: 82.0%

ethyl 2-oxopyrrolidine-5-carboxylate (66183-71-9) → Ethyl 5-Thioxopyrrolidine-2-carboxylate (84911-17-1)

Guidance literature:

With Lawessons reagent; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1016/j.tetlet.2003.12.021

Reference yield:

Ethyl 5-Thioxopyrrolidine-2-carboxylate (84911-17-1) → p-Nitrobenzyl (+/-)-6-Ethylcarbapenam-3-carboxylate (84911-32-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 61 percent / NaHCO₃ / CH₂Cl₂ / 36 h / Heating

2: 39 percent / H₂ / PtO₂ / acetic acid; trifluoroacetic acid / 24 h / 3040 Torr / Ambient temperature

3: KOH / H₂O / 12 h / Ambient temperature

4: 86 percent / H₂O / 2-methyl-propan-2-ol / 18 h

With potassium hydroxide; water; hydrogen; sodium hydrogencarbonate; platinum(IV) oxide; In dichloromethane; water; acetic acid; trifluoroacetic acid; tert-butyl alcohol;

DOI:10.1021/jo00157a010

Reference yield:

Ethyl 5-Thioxopyrrolidine-2-carboxylate (84911-17-1) → p-Nitrobenzyl (+/-)-6-Ethylcarbapenam-3-carboxylate (84984-92-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 61 percent / NaHCO₃ / CH₂Cl₂ / 36 h / Heating

2: 39 percent / H₂ / PtO₂ / acetic acid; trifluoroacetic acid / 24 h / 3040 Torr / Ambient temperature

3: KOH / H₂O / 12 h / Ambient temperature

4: 86 percent / H₂O / 2-methyl-propan-2-ol / 18 h

With potassium hydroxide; water; hydrogen; sodium hydrogencarbonate; platinum(IV) oxide; In dichloromethane; water; acetic acid; trifluoroacetic acid; tert-butyl alcohol;

DOI:10.1021/jo00157a010

upstream raw materials:

ethyl 2-oxopyrrolidine-5-carboxylate

Downstream raw materials:

2-<1-(tert-butoxycarbonyl)-2-(p-nitrobenzyloxycarbonyl)-5-pyrrolidinyl>butanoic acid

(2S,5R)-5-[(S)-1-(4-Nitro-benzyloxycarbonyl)-propyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

(2S,5R)-5-((S)-1-Methoxycarbonyl-propyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-(4-nitro-benzyl) ester

(2S,5R)-5-[(S)-1-(4-Nitro-benzyloxycarbonyl)-propyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Refernces

• 1、 Bachi, Mario D.,Breiman, Ron,Meshulam, Haim. "Synthesis of the Carbapenam System from Glutamic Acid and Acetoacetic Acid Derivatives". . p. 1439 - 1444. Retrieved 2007/10/02.