(S)-1-Cbz-pyrrolidine-3-carboxylic acid

Base Information

• Chemical Name: (S)-1-Cbz-pyrrolidine-3-carboxylic acid
• CAS No.: 192214-00-9
• Molecular Formula: C13H15NO4
• Molecular Weight: 249.266
• Hs Code.: 2933990090
• Mol file: 192214-00-9.mol

Synonyms:1,3-Pyrrolidinedicarboxylicacid, 1-(phenylmethyl) ester, (S)-;

Chemical Property of (S)-1-Cbz-pyrrolidine-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 3.06E-08mmHg at 25°C
• Melting Point: 96-98 °C
• Refractive Index: 1.582
• Boiling Point: 432.3 °C at 760 mmHg
• PKA: 4.46±0.20(Predicted)
• Flash Point: 215.3 °C
• PSA: 66.84000
• Density: 1.309 g/cm³
• LogP: 1.66760
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

(S)-1-Cbz-pyrrolidine-3-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-1-Cbz-pyrrolidine-3-carboxylic acid

There total 24 articles about (S)-1-Cbz-pyrrolidine-3-carboxylic acid 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: 90.0%

-(+)-methanol (124391-76-0) → (S)-1-((benzyloxy)carbonyl)pyrrolidine-3-carboxylic acid (192214-00-9)

Guidance literature:

With chromium(VI) oxide; In acetone; at 0 ℃;

DOI:10.1021/jo9701905

Reference yield: 82.0%

benzyl (3S)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate (865704-61-6) → (S)-1-((benzyloxy)carbonyl)pyrrolidine-3-carboxylic acid (192214-00-9)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 0 ℃; for 2.5h;

DOI:10.1055/s-2005-865362

Reference yield: 67.0%

benzyl chloroformate (501-53-1,94274-21-2) + (+)-(S)-3-cyanopyrrolidine-1-carboxylic acid benzyl ester (193693-69-5) → (S)-1-((benzyloxy)carbonyl)pyrrolidine-3-carboxylic acid (192214-00-9)

Guidance literature:

(+)-(S)-3-cyanopyrrolidine-1-carboxylic acid benzyl ester; With hydrogenchloride; water; for 4.5h; Reflux;

benzyl chloroformate; With sodium carbonate; In water; acetone; at 0 - 20 ℃; for 7h;

With hydrogenchloride; potassium hydrogensulfate; In water; pH=2;

upstream raw materials:

(+)-(S)-3-cyanopyrrolidine-1-carboxylic acid benzyl ester

-(+)-methanol

benzyl (3S)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate

(3S)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-({[(benzyloxy)carbonyl]amino}methyl)-4-oxobutanoic acid

Downstream raw materials:

(S)-(+)-3-pyrrolidinecarboxylic acid

C₁₇H₁₈N₂O₆

C₁₅H₁₉N₃O₄

(+)-(S)-3-carbamidopyrrolidine-1-carboxylic acid benzyl ester

Refernces

• 1、 -. "CARBAPENEM ANTIBACTERIALS WITH GRAM-NEGATIVE ACTIVITY". . . Retrieved 2012/01/06.
• 2、 Stoncius, Arvydas,Nahrwold, Markus,Sewald, Norbert. "Chiral succinate: A precursor for enantiomerically pure β2-amino acids". . p. 1829 - 1837. Retrieved 2007/10/03.