trans-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)-L-proline

Base Information

• Chemical Name: trans-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)-L-proline
• CAS No.: 96034-57-0
• Molecular Formula: C13H14N2O7
• Molecular Weight: 310.263
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID60441879
• Nikkaji Number: J827.723K
• Wikidata: Q72494505
• Mol file: 96034-57-0.mol

Synonyms:96034-57-0;TRANS-4-HYDROXY-1-(4-NITROBENZYLOXYCARBONYL)-L-PROLINE;(2S,4R)-4-Hydroxy-1,2-pyrrolidinedicarboxylic Acid 1-(4-Nitrobenzyl) Ester;(2S,4R)-1-((4-Nitrobenzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid;(2S,4R)-4-hydroxy-1-[(4-nitrophenyl)methoxycarbonyl]pyrrolidine-2-carboxylic Acid;(2S,4R)-4-Hydroxy-1-(((4-nitrobenzyl)oxy)carbonyl)pyrrolidine-2-carboxylic acid;SCHEMBL5391199;DTXSID60441879;MFCD16294320;(2S,4R)-4-Hydroxy-1,2-pyrrolidinedicarboxylic acid 1-(4-Nitrobenzyl)ester;AKOS025402689;(2S-trans)-4-Hydroxy-1,2-pyrrolidinedicarboxylic Acid 1-[(4-Nitrophenyl)methyl] Ester;BS-50279;N-p-nitrobenzyloxycarbonyl-L-hydroxyproline;trans-1-p-nitrobenzyloxycarbonyl-4-hydroxy-L-proline;(2S,4R)-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)proline;1-(p-Nitrobenzyloxycarbonyl)-trans-4-hydroxy-L-proline;N-(p-nitrobenzyloxycarbonyl)-trans-4-hydroxy-l-proline;trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline;trans-4-hydroxy-1-(4-nitro-benzyloxycarbonyl)-L-proline;(4R)-4-Hydroxy-1-{[(4-nitrophenyl)methoxy]carbonyl}-L-proline;(2S,4R)-4-Hydroxy-1,2-pyrrolidinedicarboxylicAcid1-(4-Nitrobenzyl)Ester;(2S,4R)-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid;(2S,4R)-4-HYDROXY-1-{[(4-NITROPHENYL)METHOXY]CARBONYL}PYRROLIDINE-2-CARBOXYLIC ACID

Chemical Property of trans-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)-L-proline

Chemical Property:

• Melting Point: 182-183℃
• Boiling Point: 578.308 °C at 760 mmHg
• PKA: 3.69±0.40(Predicted)
• Flash Point: 303.55 °C
• PSA: 132.89000
• Density: 1.558 g/cm³
• LogP: 1.21230
• Storage Temp.: Refrigerator
• Solubility.: Dichloromethane (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 310.08010079
• Heavy Atom Count: 22
• Complexity: 442

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2S,4R)-4-Hydroxy-1,2-pyrrolidinedicarboxylicAcid1-(4-Nitrobenzyl)Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(CN(C1C(=O)O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])O
• Isomeric SMILES: C1[C@H](CN([C@@H]1C(=O)O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])O
• Uses: Intermediate in the production of Meropenem.

Technology Process of trans-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)-L-proline

There total 3 articles about trans-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)-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: 98.0%

4R-4-hydroxyproline (51-35-4,30724-02-8) + 4-nitrobenzyl chloroformate (4457-32-3) → (2S,4R)-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid (96034-57-0)

Guidance literature:

With sodium hydroxide; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0960-894X(99)00646-0

Reference yield: 70.0%

→ (2S,4R)-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid (96034-57-0)

Guidance literature:

Reference yield:

4-nitrobenzyl chloride (619-73-8) → (2S,4R)-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid (96034-57-0)

Guidance literature:

Multi-step reaction with 2 steps

1: dioxane

2: aqueous NaOH; dioxane

With 1,4-dioxane; sodium hydroxide;

DOI:10.1021/ja01135a030

upstream raw materials:

4R-4-hydroxyproline

4-nitrobenzyl chloroformate

4-nitrobenzyl chloride

Downstream raw materials:

trans-4-chloroacetoxy-1-(4-nitro-benzyloxycarbonyl)-L-proline

(2S,4R)-1-(p-Nitrobenzyloxycarbonyl)-4-hydroxyprolinanilide

(2S,4R)-1-p-nitrobenzyloxycarbonyl-4-methanesulfonyloxy-2-pyrrolidinethiocarboxylic acid

4-Nitrobenzyl (2S,4R)-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylate

Refernces

• 1、 -. "Meropenem side chain intermediate and method for preparing same". Paragraph 0048-0050; 0055-0057. . Retrieved 2019/01/23.
• 2、 Hoen, Rob,Novoa, Eva Maria,López, Alba,Camacho, Noelia,Cubells, Laia,Vieira, Pedro,Santos, Manuel,Marin-Garcia, Patricia,Bautista, Jose Maria,Cortés, Alfred,Ribas de Pouplana, Lluís,Royo, Miriam. "Selective Inhibition of an Apicoplastic Aminoacyl-tRNA Synthetase from Plasmodium falciparum". . p. 499 - 509. Retrieved 2013/05/09.