3057-74-7

Basic information

• Product Name: L-Aspartic acid 4-tert-butyl ester
• Synonyms: ASPARTIC ACID BETA T-BUTYL ESTER MONOHYDRATE;ASPARTIC ACID(OTBU);H-ASP(OBUT)-OH;H-ASP(OTBU)-OH;H-L-ASP(OTBU)-OH;H-L-ASP(TBU)-OH H2O;L-ASPARTIC ACID 4-TERT-BUTYL ESTER;L-ASPARTIC ACID B-TERT-BUTYL ESTER
• CAS NO: 3057-74-7
• Molecular Formula: C₈H₁₅NO₄
• Molecular Weight: 189.21
• EINECS: 221-292-8
• Product Categories: Amino Acids Derivatives;Amino Acids;Aspartic acid [Asp, D];Amino Acids and Derivatives;Amino Acid Derivatives;Aspartic Acid;Peptide Synthesis
• Mol File: 3057-74-7.mol

Chemical Properties

• Melting Point: 220°C (dec.)
• Boiling Point: 318.7 °C at 760 mmHg
• Flash Point: 146.5 °C
• Appearance: /
• Density: 1.162 g/cm³
• Vapor Pressure: 7.48E-05mmHg at 25°C
• Refractive Index: 1.475
• Storage Temp.: 2-8°C
• Solubility: Methanol (Slightly), Water (Slightly, Sonicated)
• PKA: 2.19±0.23(Predicted)
• Stability: Hygroscopic
• BRN: 4671089
• CAS DataBase Reference: L-Aspartic acid 4-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Aspartic acid 4-tert-butyl ester(3057-74-7)
• EPA Substance Registry System: L-Aspartic acid 4-tert-butyl ester(3057-74-7)

Safety Data

• Statements: 36/37/38
• Safety Statements: 22-24/25-44-35-28-7-4
• WGK Germany: 3
• Hazardous Substances Data: 3057-74-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
L-Aspartic acid 4-tert-butyl ester is used as an intermediate in the synthesis of various pharmaceutical compounds for its ability to protect the L-Aspartic acid moiety during chemical reactions. This protection is essential for the successful synthesis of complex molecules with specific biological activities.
Used in Neurochemistry Research:
As a modulator of membrane conductance in mammalian neurons, L-Aspartic acid 4-tert-butyl ester is used as a research tool to study the mechanisms underlying neuronal depolarization and nerve impulse transmission. This application aids in understanding the fundamental processes of the central nervous system and can contribute to the development of treatments for neurological disorders.
Used in Amino Acid Biosynthesis:
L-Aspartic acid 4-tert-butyl ester serves as a protected form of L-Aspartic acid, which is used as a building block in the biosynthesis of other amino acids. This makes it an essential component in the production of amino acids required for various biological processes, including protein synthesis and metabolic functions.
Used in Chemical Synthesis:
Due to its protective nature, L-Aspartic acid 4-tert-butyl ester is utilized in chemical synthesis to facilitate the production of complex molecules with specific functionalities. This application is particularly relevant in the development of new drugs, materials, and other specialty chemicals that require the precise incorporation of L-Aspartic acid.

InChI:InChI=1/C8H15NO4/c1-8(2,3)13-6(10)4-5(9)7(11)12/h5H,4,9H2,1-3H3,(H,11,12)/t5-/m1/s1

Upstream product

• 27486-72-2 Z-L-Asp(β-O-t-Bu)-ONb 
• 5545-52-8 Z-D(tBu)-OH 
• 36702-55-3 (S)-2-Benzyloxycarbonylamino-succinic acid 4-tert-butyl ester 1-ethyl ester 
• 63276-59-5 L-aspartic acid β-tert-butyl ester α-ethyl ester 
• 71989-14-5 Fmoc-(tBu)Asp-OH 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 115-11-7 isobutene 
• 1791-13-5 L-aspartic acid di-tert-butyl ester hydrochloride 
• 127556-07-4 (2R)-N-<(2S)-2-<amino>-3-<(tert-butyl)oxycarbonyl>propan-1-oyl>bornane-10,2-sultam 
• 2131-29-5 (S)-1-benzyl-4-tert-butyl 2-aminosuccinate 

Downstream Products

• 1676-90-0 Boc-Asp(OtBu)-OH 
• 136213-10-0 Z-L-Phe-L-Asp(OtBu)-OH 
• 119439-55-3 (S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-succinic acid 4-tert-butyl ester 
• 71989-14-5 Fmoc-(tBu)Asp-OH 
• 152548-66-8 (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid 
• 3408-50-2 [(N-benzyloxycarbonyl)-L-alaninyl]-L-aspartic acid [beta]-tert-butyl ester 
• 158641-91-9 NVOC-Asp(tBu)-OH 
• 482632-06-4 2-(9-phenyl-9H-fluoren-9-ylamino)-succinic acid 4-tert-butyl ester 
• 153287-86-6 (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid tert-butyl ester 
• 1393721-13-5 (S)-tert-butyl 4-(benzyl(methyl)amino)-3-(tert-butoxycarbonylamino)butanoate 
• 1147996-31-3 C₆₈H₁₀₃N₉O₁₅S₂ 

Relevant articles and documents

Preparation method of N -fluorenylmethoxycarbonyl - L -aspartic -4 -tert-butyl ester

The invention relates to the technical field of organic synthesis, in particular to a preparation method of a fluorenylmethoxycarbonyl - aspartic -4 - tert-butyl ester, which comprises the following specific steps: L - aspartic acid is used as a starting raw material, L - aspartic acid internal anhydride hydrochloride is obtained through dehydration treatment of phosphorus trichloride. L- Aspartic acid ester hydrochloride and ethanol were subjected to alcoholysis to obtain L -aspartate hydrochloride. The transesterification reaction L-aspartate and tert-butyl ester gives L -butyl-1 -ethyl-4 -butyl acrylate. Further hydrolysis L-butyl-1 - ethyl ester -4 - gives L -butyl-4 -tert-butyl ester. The L-aspartate -4 - tert-butyl ester is reacted with the fluorenylmethoxycarbonyl reagent to obtain the target product fluorenylmethoxycarbonyl - aspartic -4 -tert-butyl ester. The preparation method of the fluorenylmethoxycarbonyl - aspartic -4 - tert-butyl ester provided by the invention is safe and environment-friendly in production process and suitable for industrial large-scale production.

Gold-Catalyzed Amide/Carbamate-Linked N, O-Acetal Formation with Bulky Amides and Alcohols

A gold-catalyzed N,O-acetal formation was established to construct an amide/carbamate-linked N,O-acetal substructure with bulky alcohols. The acyliminium cation species generated from o-alkynylbenzoic acid ester in the presence of a gold catalyst is highly reactive and underwent nucleophilic attack of various bulky alcohols and phenols at room temperature under neutral conditions, leading to the corresponding N,O-acetals in yields of 34-89% with good functional group tolerance.

A mild removal of Fmoc group using sodium azide

A mild method for effectively removing the fluorenylmethoxycarbonyl (Fmoc) group using sodium azide was developed. Without base, sodium azide completely deprotected Nα-Fmoc-amino acids in hours. The solvent-dependent conditions were carefully studied and then optimized by screening different sodium azide amounts and reaction temperatures. A variety of Fmoc-protected amino acids containing residues masked with different protecting groups were efficiently and selectively deprotected by the optimized reaction. Finally, a biologically significant hexapeptide, angiotensin IV, was successfully synthesized by solid phase peptide synthesis using the developed sodium azide method for all Fmoc removals. The base-free condition provides a complement method for Fmoc deprotection in peptide chemistry and modern organic synthesis. Graphical Abstract: [Figure not available: see fulltext.]

Reliable and safe, gram-scale hydrogenation and hydrogenolysis of O-benzyl ether groups with in situ Pd0/C catalyst

Hydrogenation of alkenes, alkynes, and hydrogenolysis of O-benzyl ethers with Pd0/C catalyst generated in situ can be readily scaled up under safer conditions than with traditional procedures. The precise control of the palladium loading and the mild conditions developed allow the formation of a very active and reliable Pd0/C catalyst, leading to highly reproducible results. Georg Thieme Verlag Stuttgart - New York.

A useful, reliable and safer protocol for hydrogenation and the hydrogenolysis of o-benzyl groups: The in situ preparation of an active Pd 0/C catalyst with well-defined properties

A simple, highly reproducible protocol for the hydrogenation of alkenes and alkynes and for the hydrogenolysis of O-benzyl ethers has been developed. The method features the in situ preparation of an active Pd0/C catalyst from Pd(OAc)2 and charcoal, in methanol. The mild reaction conditions (25°C) and low catalyst loading required (0.025 mol%), as well as the absence of contamination of the product by palladium residues (0/C: It's a kind of magic! A sustainable, simple and highly reproducible protocol for the hydrogenation of alkenes and alkynes (see scheme) and for the hydrogenolysis of O-benzyl ethers has been developed with an in situ generated Pd0/C catalyst. The homemade Pd0/C catalyst allows mild reaction conditions (25°C, 1 atm H2) and low catalyst loading (as low as 0.025 mol%), without any contamination of the product by palladium residues (4 ppb).

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.

Selective Deprotection of the Nα-tert-Butyloxycarbonyl Group in Solid Phase Peptide Synthesis with Chlorotrimethylsilane and Phenol

The repetitive deprotection of the Nα-tert-butyloxycarbonyl group during solid phase peptide synthesis was found to be efficient and quantitative by use of a mild new reagent containing 1 M chlorotrimethylsiane and 1 M phenol in dichloromethane.Kinetic studies showed that the half-life for the reaction at 22 deg C with Boc-Val-resin was 17.5 min, a 40-fold increase over the rate in the absence of phenol.The reaction is not due to the presence of HCl in the reagent.The selectivity between the removal at the Nα-tert-butyloxycarbonyl group and benzylic esters, ethers, and carbonate side chain protecting groups was >1E5 and relative to the anchoring benzyl ester bond to the resin support it was 6E3.This is a marked improvement over the selectivity of the conventional 50percent trifluoroacetic acid in CH2Cl2 deprotecting agent and significantly reduces the accumulated byproducts resulting from losses of benzylic groups.The cleavage of the tert-butyl urethane was first order in Me3SiCl and second order in C6H5OH.The preferred reagent is 1 M Me3SiCl-3 M C6H5OH-CH2Cl2 and the deprotection time is 20 min (t1/2 = 1.8 min for Boc-Val-OCH2-resin).Evidence for the mechanism of the reaction was deduced.Several peptides, including Leu-enkephalin, -angiotensin II, and glucagon were successfully synthesized in high yields and excellent purity by the stepwise solid phase method using this new reagent.

ASYMMETRIC ALKYLATIONS OF A SULTAM-DERIVED GLYCINATE EQUIVALENT: PRACTICAL PREPARATION OF ENANTIOMERICALLY PURE α-AMINO ACIDS

Deprotonation/alkylation of sultam-derived N-glycinate equivalent 3 gave crystalline products 5 which on mild hydrolysis furnished α-amino acids 7 (ca.100percent e.e.) in high overall yield.