2419-56-9

Basic information

• Product Name: L-Glutamic acid 5-tert-butyl ester
• Synonyms: L-Glutamic acid 5-te;Glu(OtBu);H-L-Glu(OtBu)-OH;(2S)-2-Amino-5-tert-butoxy-5-oxopentanoic acid;H-Glu(OtBu)-OH·H2O L-GlutaMic acid γ-tert·butyl ester Monohydrate;5-tert-Butyl L-GlutaMate;5-tert-Butyl L-GlutaMate Hydrate;(S)-2-aMino-5-(tert-butoxy)-5-oxopentanoic acid
• CAS NO: 2419-56-9
• Molecular Formula: C₉H₁₇NO₄
• Molecular Weight: 203.24
• EINECS: 247-005-6
• Product Categories: Amino Acids;Glutamic acid [Glu, E];Amino Acids and Derivatives;Amino Acid Derivatives;Glutamic Acid;Peptide Synthesis
• Mol File: 2419-56-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 182°C(lit.)
• Boiling Point: 336.4 °C at 760 mmHg
• Flash Point: 157.3 °C
• Appearance: /Solid
• Density: 1.133 g/cm³
• Vapor Pressure: 2.11E-05mmHg at 25°C
• Refractive Index: 1.475
• Storage Temp.: 2-8°C
• PKA: 2.20±0.10(Predicted)
• Water Solubility: Sparingly soluble in water; practically insoluble in ethanol or ether.
• BRN: 2049031
• CAS DataBase Reference: L-Glutamic acid 5-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Glutamic acid 5-tert-butyl ester(2419-56-9)
• EPA Substance Registry System: L-Glutamic acid 5-tert-butyl ester(2419-56-9)

Safety Data

• Statements: 22-24
• Safety Statements: 22-24/25-25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 2419-56-9(Hazardous Substances Data)

Usage

Chemical Properties

White powder crystal

Uses

L-Glutamic acid 5-tert-butyl ester is used as a fine chemical intermediate, pharmaceutical intermediate.

InChI:InChI=1/C9H17NO4/c1-9(2,3)14-7(11)5-4-6(10)8(12)13/h6H,4-5,10H2,1-3H3,(H,12,13)/t6-/m0/s1

Upstream product

• 32677-01-3 L-glutamic acid di-tert-butyl ester hydrochloride 
• 16874-06-9 di-tert-butyl L-glutamate 
• 56-86-0 L-glutamic acid 
• 115-11-7 isobutene 
• 71989-18-9 Fmoc-Glu(OtBu)-OH 
• 56877-41-9 methyl 2(S)-2-benzyloxycarbonylamino-4-tert-butoxycarbonylbutanoate 
• 3705-42-8 Cbz-(L)-Glu-OBn 
• 13030-09-6 1-benzyl L-glutamate 
• 3967-18-8 (S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-benzyl ester 5-tert-butyl ester 
• 47709-87-5 N-(2-)-propyl-(2)-oxycarbonyl)-glutaminsaeure-γ-tert.-butylester 
• 62188-74-3 H-Glu(O-t-Bu)-OBzl 
• 3886-08-6 5-tert-butyl N-benzyloxycarbonyl-L-glutamate 

Downstream Products

• 13155-43-6 N--L-glutaminsaeure-γ-tert.-butylester 
• 71989-18-9 Fmoc-Glu(OtBu)-OH 
• 78346-78-8 Z-L-Ile-L-Glu(OtBu)-OH 
• 1264272-63-0 5-(tert-butoxy)-2-(4-(2,7-difluoro-6-hydroxy-3-oxo-3H-xanthen-9-yl)-3-methylbenzamido)-5-oxopentanoic acid 
• 53576-52-6 N-tetradecanoyl-L-glutamic acid 
• 1221251-54-2 C₄₃H₆₇N₉O₁₁S 
• 1221251-43-9 Ac-R(Pbf)-H(Trt)-E(t-Bu)-L 
• 1221251-48-4 C₆₂H₈₁N₉O₁₁S 
• 1221251-51-9 C₆₅H₈₇N₉O₁₁S 
• 110484-34-9 Z-Thr(tBu)-Ile-Glu(OtBu)-Gln-Glu(OtBu)-OH 
• 110484-44-1 Z-Ile-Glu(OtBu)-Gln-Glu(OtBu)-OH 
• 110484-42-9 Z-Glu(OtBu)-Gln-Glu(OtBu)-OH 
• 86061-04-3 N^α-Fmoc-Glu-(O-tBu)-OPfp 

Relevant articles and documents

Synthesis of ω-tert-butyl esters of aspartic acid and glutamic acid via B,B-difluoroboroxazolidones

B,B-Difluoroboroxazolidones (DFBONs) were synthesized for the first time from salts of amino acid and BF3·Et2O, and their properties were examined. DFBONs were used in selective preparation of Glu(OBu(t)) and Asp(OBu(t)) in good yields under catalysis with BF3·Et2O and H3PO4. Amberlite XAD-2 resin was successfully employed to purify the above amino acid derivatives.

PROCESSES FOR PREPARATION OF (S)-TERT-BUTYL 4,5-DIAMINO-5-OXOPENTANOATE

Provided are processes for the preparation of (S)-tert-butyl 4,5-diamino-5-oxopentanoate, or a salt, solvate, hydrate, enantiomer, mixture of enantiomers, or isotopologue thereof. Also provided are solid forms of various intermediates and products obtained from the processes.

Mild oxidative cleavage of 9-BBN-protected amino acid derivatives

Protection of the amino acid moiety using 9-BBN is an effective method to enable side chain manipulations in synthesis of complex amino acids. We investigated the standard, mild method for deprotection of the 9-BBN group in methanolic chloroform, and found that it relies on a slow oxidation mediated by molecular oxygen. Building on this insight, we have developed a method that allows for a fast and selective deprotection using simple peroxy acid reagents. After Fmoc protection, products were isolated in >90% yield for a series of amino acid derivatives, including a galactosylated derivative of hydroxylysine. A representative set of 9-BBN-protected amino acid derivatives were efficiently deprotected using peracid reagents in excellent yields. Deprotection is orthogonal with several common protecting groups. Its tolerance of highly acid sensitive groups, such as trityl-protected amides and glycosidic linkages, is especially notable.