N-Benzyloxycarbonyl-L-proline

Base Information

• Chemical Name: N-Benzyloxycarbonyl-L-proline
• CAS No.: 1148-11-4
• Molecular Formula: C13H15NO4
• Molecular Weight: 249.266
• Hs Code.: 29339900
• European Community (EC) Number: 214-557-4
• UNII: H2BS8M5FPP
• DSSTox Substance ID: DTXSID40150856
• Nikkaji Number: J25.953E
• Wikidata: Q27896112
• ChEMBL ID: CHEMBL3276375
• Mol file: 1148-11-4.mol

Synonyms:carbobenzoxyproline;CBZ-Pro;CBZ-proline

Chemical Property of N-Benzyloxycarbonyl-L-proline

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 3.06E-08mmHg at 25°C
• Melting Point: 76-78 °C
• Refractive Index: -40 ° (C=2, EtOH)
• Boiling Point: 432.3 °C at 760 mmHg
• PKA: 3.99±0.20(Predicted)
• Flash Point: 215.3 °C
• PSA: 66.84000
• Density: 1.309 g/cm³
• LogP: 1.81010
• Storage Temp.: 2-8°C
• Solubility.: Solubility in methanol, almost transparency.
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 249.10010796
• Heavy Atom Count: 18
• Complexity: 312

Purity/Quality:

99% ^*data from raw suppliers

N-Benzyloxycarbonyl-L-proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 62-36/37/38-20/21/22
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)OCC2=CC=CC=C2)C(=O)O
• Isomeric SMILES: C1C[C@H](N(C1)C(=O)OCC2=CC=CC=C2)C(=O)O
• Uses: N-(Benzyloxycarbonyl)-L-proline is a potent in vitro and in vivo inhibitor of prolidase; a specific peptidase that cleaves dipeptides with a C-terminal prolyl and hydroxylprolyl residue. It is also used in the synthesis of N-(L-Prolyl)-β-alanine which is a derivative of the naturally occurring beta amino acid β-Alanine.

Technology Process of N-Benzyloxycarbonyl-L-proline

There total 57 articles about N-Benzyloxycarbonyl-L-proline 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: 100.0%

N-Cbz-Prolinol (6216-63-3) → N-Benzyloxycarbonyl-L-proline (1148-11-4)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid; sodium hydrogencarbonate; sodium bromide; In water; acetone; at 20 ℃; for 24h;

DOI:10.1021/jo034276b

Reference yield: 98.0%

N-carbobenzoxy-L-proline phenylmethyl ester (124980-30-9) → N-Benzyloxycarbonyl-L-proline (1148-11-4)

Guidance literature:

With palladium diacetate; sodium hydride; In N,N-dimethyl acetamide; at 50 ℃; for 5h; Inert atmosphere;

Reference yield: 98.0%

phenyl chloroformate (1885-14-9) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → N-Benzyloxycarbonyl-L-proline (1148-11-4)

Guidance literature:

With hydrogenchloride; In sodium hydroxide; toluene;

upstream raw materials:

benzyl chloroformate

L-proline

(S)-2-tert-butyl-1-benzylpyrrolidine-1,2-dicarboxylate

dibenzyl dicarbonate

Downstream raw materials:

N-benzyloxycarbonyl-L-proline p-nitrophenyl ester

benzyloxycarbonyl-L-prolin-L-valin methyl ester

N-(benzyloxycarbonyl)-L-prolyl-L-O-tyrosine methyl ester

N-[N²-(1-benzyloxycarbonyl-L-prolyl)-N⁶-(toluene-4-sulfonyl)-L-lysyl]-L-aspartic acid dimethyl ester

Refernces

• 1、 Hernandez, Jose G.,Juaristi, Eusebio. "Asymmetric aldol reaction organocatalyzed by (S)-proline-containing dipeptides: Improved stereoinduction under solvent-free conditions". . p. 1464 - 1467. Retrieved 2011.
• 2、 Berger et al.. "-". . p. 5552. Retrieved 1954.
• 3、 Hartikka, Antti,Arvidsson, Per I.. "5-(Pyrrolidine-2-yl)tetrazole: Rationale for the increased reactivity of the tetrazole analogue of proline in organocatalyzed aldol reactions". . p. 4287 - 4295. Retrieved 2005.
• 4、 Machuca, Elizabeth,Juaristi, Eusebio. "Organocatalytic activity of α,α-dipeptide derivatives of (S)-proline in the asymmetric aldol reaction in absence of solvent. Evidence for non-covalent π-π Interactions in the transition state". . p. 1144 - 1148. Retrieved 2015.
• 5、 Giletto, Matthew B.,Osmulski, Pawel A.,Jones, Corey L.,Gaczynska, Maria E.,Tepe, Jetze J.. "Pipecolic esters as minimized templates for proteasome inhibition". . p. 2734 - 2746. Retrieved 2019.
• 6、 Yang, Shyh-Chyun,Shea, Fang-Rong,Hung, Chung-Wei. "The Synthesis of 5,6,7,7a-Tetrahydro-1-methyl-3H-pyrrolizin-3-one by the Palladium-Catalyzed Cyclization of N-Bromoacetyl-2-vinylpyrrolidine". . p. 779 - 782. Retrieved 1998.
• 7、 Katakam, Nanda Kumar,Seifert, Cole W.,D'Auria, John,Li, Guigen. "Efficient synthesis of methyl (S)-4-(1-methylpyrrolidin-2-YL)-3-oxobutanoate as the key intermediate for tropane alkaloid biosynthesis with optically acitve form". . p. 604 - 613. Retrieved 2019/08/01.