L-Glutamic acid, N-[N-[(phenylmethoxy)carbonyl]-L-a-glutamyl]-, triethyl ester

Base Information

• Chemical Name: L-Glutamic acid, N-[N-[(phenylmethoxy)carbonyl]-L-a-glutamyl]-, triethyl ester
• CAS No.: 3523-22-6
• Molecular Formula: C24H34N2O9
• Molecular Weight: 494.542
• Mol file: 3523-22-6.mol

Synonyms:

Chemical Property of L-Glutamic acid, N-[N-[(phenylmethoxy)carbonyl]-L-a-glutamyl]-, triethyl ester

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Glutamic acid, N-[N-[(phenylmethoxy)carbonyl]-L-a-glutamyl]-, triethyl ester

There total 7 articles about L-Glutamic acid, N-[N-[(phenylmethoxy)carbonyl]-L-a-glutamyl]-, triethyl ester 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: 53.2%

(S)-2-Amino-pentanedioic acid 5-ethyl ester (1119-33-1) + diethyl-L-glutamate hydrochloride (1118-89-4) + benzyl chloroformate (501-53-1,94274-21-2) → (2S)-2-[(2S)-2-carboxybenzylamino-4-(ethoxycarbonyl)butanoyl]aminopentanedioic acid diethyl ester (3523-22-6)

Guidance literature:

(S)-2-Amino-pentanedioic acid 5-ethyl ester; benzyl chloroformate; With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

diethyl-L-glutamate hydrochloride; In N,N-dimethyl-formamide; for 24h;

DOI:10.3390/molecules200610004

Reference yield:

ethanol (64-17-5) + N-(N-benzyloxycarbonyl-α-L-glutamyl)-L-glutamic acid-5-ethyl ester → (2S)-2-[(2S)-2-carboxybenzylamino-4-(ethoxycarbonyl)butanoyl]aminopentanedioic acid diethyl ester (3523-22-6)

Guidance literature:

With toluene-4-sulfonic acid; at 20 ℃;

DOI:10.1021/ja01175a012

Reference yield:

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → (2S)-2-[(2S)-2-carboxybenzylamino-4-(ethoxycarbonyl)butanoyl]aminopentanedioic acid diethyl ester (3523-22-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogenchloride / 48 h / 20 °C

2.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C

2.2: 24 h

With hydrogenchloride; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide;

DOI:10.3390/molecules200610004

upstream raw materials:

ethanol

(S)-2-(benzyloxycarbonylamino)-5-ethoxy-5-oxopentanoic acid

diethyl-L-glutamate hydrochloride

(S)-2-Amino-pentanedioic acid 5-ethyl ester

Downstream raw materials:

N-[O-ethyl-N-(O-ethyl-N-benzyloxycarbonyl-L-α-glutamyl)-L-α-glutamyl]-L-glutamic acid diethyl ester

N-(N-benzyloxycarbonyl-L-α-glutamyl)-glutamic acid

L-glutamyl-L-glutamic acid