2-(((Benzyloxy)carbonyl)amino)-5-methoxy-5-oxopentanoic acid

Base Information

• Chemical Name: 2-(((Benzyloxy)carbonyl)amino)-5-methoxy-5-oxopentanoic acid
• CAS No.: 4652-65-7
• Molecular Formula: C14H17NO6
• Molecular Weight: 295.292
• Hs Code.: 2924299090
• NSC Number: 88483
• Nikkaji Number: J2.659.324G
• Mol file: 4652-65-7.mol

Synonyms:2-(((Benzyloxy)carbonyl)amino)-5-methoxy-5-oxopentanoic acid;Z-L-Glu(Me)-OH;(2S)-5-methoxy-5-oxo-2-(phenylmethoxycarbonylamino)pentanoic acid;NSC88483;5-methoxy-5-oxo-2-(phenylmethoxycarbonylamino)pentanoic acid;NCIOpen2_005487;SCHEMBL5970693;NSC-88483;STL323152;AKOS015916333;FT-0653085;FT-0688456;2-{[(benzyloxy)carbonyl]amino}-5-methoxy-5-oxopentanoic acid (non-preferred name)

Chemical Property of 2-(((Benzyloxy)carbonyl)amino)-5-methoxy-5-oxopentanoic acid

Chemical Property:

• Vapor Pressure: 3.01E-11mmHg at 25°C
• Melting Point: 76℃
• Refractive Index: 1.535
• Boiling Point: 510.6 °C at 760 mmHg
• Flash Point: 262.6 °C
• PSA: 101.93000
• Density: 1.272 g/cm³
• LogP: 1.71010
• Storage Temp.: -15°C
• Solubility.: soluble in Methanol
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 295.10558726
• Heavy Atom Count: 21
• Complexity: 365

Purity/Quality:

98% ^*data from raw suppliers

Z-L-glutamic acid γ-methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)CCC(C(=O)O)NC(=O)OCC1=CC=CC=C1
• Uses: Z-Glu(OMe)-OH is an inhibitor of fibrin stabilizing factor.

Technology Process of 2-(((Benzyloxy)carbonyl)amino)-5-methoxy-5-oxopentanoic acid

There total 16 articles about 2-(((Benzyloxy)carbonyl)amino)-5-methoxy-5-oxopentanoic 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: 100.0%

L-glutamic acid 5-methyl ester (1499-55-4) + benzyl chloroformate (501-53-1,94274-21-2) → (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-methyl ester (4652-65-7)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 0 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.9b04479

Reference yield: 99.0%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + γ-methyl L-glutamate hydrochloride (3077-51-8) → (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-methyl ester (4652-65-7)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; for 15h;

DOI:10.1055/s-0040-1707146

Reference yield: 89.0%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + L-glutamic acid 5-methyl ester (1499-55-4) → (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-methyl ester (4652-65-7)

Guidance literature:

With potassium carbonate; In water; acetone; for 1.5h; Ambient temperature;

DOI:10.1016/0040-4020(95)00455-H

upstream raw materials:

L-glutamic acid 5-methyl ester

sodium methylate

N-(benzyloxycarbonyl)-L-glutamic acid anhydride

methanol

Downstream raw materials:

1-tert-butyl 5-methyl (2S)-2-{[(benzyloxy)carbonyl]amino}pentanedioate

(S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester

benzyloxycarbonyl-L-glutamic acid α-tert-butyl ester γ-hydrazide

γ-methyl-α-tert-butyl ester of N-carbobenzoxyglutamic acid

Refernces

• 1、 Kabes, Connor Q.,Gunn, Jack H.,Selbst, Maximilian A.,Lucas, Reagan F.,Gladysz, John A.. "Syntheses of Enantiopure 1,2-Ethylenediamines with Tethered Secondary Amines of the Formula H 2NCH 2CH[(CH 2) nNHMe]NH 2(n = 1-4) from α-Amino Acids: New Agents for Asymmetric Catalysis". . p. 3277 - 3285. Retrieved 2020/11/02.
• 2、 -. "METHOD FOR PREPARING 3-[(4S)-8-BROMO-1-METHYL-6-(PYRIDIN-2-YL)-4H-IMIDAZO[1,2-A][1,4]BENZODIAZEPIN-4-YL]-PROPIONIC ACID METHYL ESTER, AND COMPOUNDS USEFUL IN SAID METHOD". Page/Page column 34; 35. . Retrieved 2019/05/02.