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

Base Information

• Chemical Name: (2S,4R)-4-benzyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic Acid
• CAS No.: 153074-95-4
• Molecular Formula: C17H23 N O4
• Molecular Weight: 305.374
• DSSTox Substance ID: DTXSID10521019
• Mol file: 153074-95-4.mol

Synonyms:(2S,4R)-4-benzyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic Acid;4-benzyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid;1229439-64-8;MFCD07784045;SCHEMBL7285245;(2R,4R)-4-benzyl-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid;(2R,4S)-4-benzyl-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid;(2S,4S)-4-benzyl-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid;DTXSID10521019;AB42876;AB42880;4-Benzyl-1-(tert-butoxycarbonyl)proline;SY278929;A809931;4-benzyl-1-tert-butoxycarbonyl-pyrrolidine-2-carboxylic acid

Chemical Property of (2S,4R)-4-benzyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic Acid

Chemical Property:

• Melting Point: 100-102℃
• Boiling Point: 447.9±38.0 °C(Predicted)
• PKA: 4.01±0.40(Predicted)
• PSA: 66.84000
• Density: 1.185±0.06 g/cm3(Predicted)
• LogP: 2.87720
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 305.16270821
• Heavy Atom Count: 22
• Complexity: 409

Purity/Quality:

98%min ^*data from raw suppliers

Boc-rans-4-benzyl-L-proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1C(=O)O)CC2=CC=CC=C2

Technology Process of (2S,4R)-4-benzyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic Acid

There total 19 articles about (2S,4R)-4-benzyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-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: 92.0%

ethyl (2S,4R)-N-BOC-4-benzylprolinate (171038-43-0) → (2S,4R)-4-benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (153074-95-4,158459-13-3)

Guidance literature:

With lithium hydroxide; In methanol; at 20 ℃; for 18h;

DOI:10.1016/j.bmcl.2005.03.120

Reference yield: 86.0%

(2S,4R)-N-tert-butyloxycarbonyl-4-benzyl-2-hydroxymethylpyrrolidine (540501-43-7) → (2S,4R)-4-benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (153074-95-4,158459-13-3)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; NaH₂PO₄ buffer; sodium hypochlorite; In water; acetonitrile; at 45 ℃; for 24h; pH=6.6;

DOI:10.1021/jo034214l

Reference yield: 60.0%

→ (2S,4R)-4-benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (153074-95-4,158459-13-3)

Guidance literature:

upstream raw materials:

(2S,4R)-N-tert-butyloxycarbonyl-4-benzyl-2-hydroxymethylpyrrolidine

ethyl (2S,4R)-N-BOC-4-benzylprolinate

di-tert-butyl dicarbonate

tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate

Downstream raw materials:

(2S,4R)-4-Benzyl-2-(3-phenyl-propylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4R)-4-Benzyl-2-phenethylcarbamoyl-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4R)-4-Benzyl-2-(4-methoxy-benzylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4R)-4-Benzyl-2-phenylcarbamoyl-pyrrolidine-1-carboxylic acid tert-butyl ester