3588-63-4

Basic information

• Product Name: N-CARBOBENZOXY-DL-VALINE
• Synonyms: Z-DL-VALINE extrapure;(±)-N-[(Phenylmethoxy)carbonyl]valine;N-[(Phenylmethoxy)carbonyl]-DL-valine;2-(benzyloxycarbonylamino)-3-methyl-butyric acid;N-Cbz-DL-valine Z-DL-Val-OH;Z-DL-Val;Cbz-DL-valine;DL-Cbz valine
• CAS NO: 3588-63-4
• Molecular Formula: C₁₃H₁₇NO₄
• Molecular Weight: 251.28
• EINECS: 222-727-4
• Product Categories: Cbz-Amino Acids;Amino Acids;Amino Acids (N-Protected);Biochemistry
• Mol File: 3588-63-4.mol

Chemical Properties

• Melting Point: 78 °C
• Boiling Point: 432.6 °C at 760 mmHg
• Flash Point: 215.4 °C
• Appearance: Off-white to white/Powder
• Density: 1.182 g/cm³
• Storage Temp.: 2-8°C
• Solubility: almost transparency in Methanol
• CAS DataBase Reference: N-CARBOBENZOXY-DL-VALINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-CARBOBENZOXY-DL-VALINE(3588-63-4)
• EPA Substance Registry System: N-CARBOBENZOXY-DL-VALINE(3588-63-4)

Safety Data

• Statements: 52/53
• Safety Statements: 61-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 3588-63-4(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

InChI:InChI=1/C13H17NO4/c1-9(2)11(12(15)16)14-13(17)18-8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3,(H,14,17)(H,15,16)

Upstream product

• 516-06-3 D,L-valine 
• 501-53-1 benzyl chloroformate 
• 100-51-6 benzyl alcohol 
• 20314-88-9 tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate 
• 91806-74-5 3,5-dimethyl-pyrazole-1-carboxylic acid benzyl ester 

Downstream Products

• 134306-34-6 N-(Benzyloxycarbonyl)valine methyl ester 
• 879123-73-6 N-(N-benzyloxycarbonyl-valyl)-alanine ethyl ester 
• 105120-38-5 N-(N-benzyloxycarbonyl-valyl)-phenylalanine ethyl ester 
• 115020-46-7 N-(N-benzyloxycarbonyl-valyl)-thioglycine S-phenyl ester 
• 1999-88-8 methyl (S)-2-((S)-2-benzyloxycarbonyl-amino-3-methylbutyrylamino)-3-methylbutyrate 
• 32402-29-2 N-benzyloxycarbonyl-D-valyl-L-valine methyl ester 
• 879553-76-1 N-(N-benzyloxycarbonyl-valyl)-valine ethyl ester 
• 72635-90-6 Z-L-Val-D-Val-OMe 
• 106561-19-7 Z-D-valyl-D-valine methyl ester 
• 56610-23-2 N-BZO-val-gly-gly 
• 17708-79-1 N-(N-benzyloxycarbonyl-valyl)-leucine 
• 4817-93-0 N-(N-benzyloxycarbonyl-valyl)-leucine methyl ester 
• 16770-04-0 N-(N-benzyloxycarbonyl-Ξ-valyl)-D-glutamic acid diethyl ester 
• 56694-30-5 N-(N-benzyloxycarbonyl-Ξ-valyl)-L-leucine ethyl ester 

Relevant articles and documents

Chiral tetraaryl-and tetraalkynylborates as chiral solvating agents for tetraalkylammonium salts

The application of tetracarbon-substituted chiral borate sodium salts (NaBR*4) as NMR chiral solvating agents for various tetraalkylammonium salts (R4NX) has been successfully demonstrated. Ion exchange between R4NX and NaBR*4 proceeded in excellent yields and provided the corresponding dia-stereomeric salts (R4NBR*4). The ee values of the R4NX salts were determined by1H NMR analysis of R4NBR*4. Two types of chiral borates, tetraaryl-and tetraalkynylborates with optically active 1,1′-binaphthyl components were used. At the beginning of this research, we investigated the efficacy of a known chiral tetraar-ylborate developed by Pommerening et al. for R4NX. To expand the possibility of further structural design of the chiral borate, we designed chiral tetraalkynylborates as a new structure. Their synthesis and application are also described.

A Stereoselective entry into functionalized 1,2-diamines by zinc-mediated homologation of α-aminoacids

A general, stereoselective synthsis of 4,5-disubstituted imidazolidines-2-ones from α-aminoacids has been developed: the key steps are a Biaise reaction of bromoacetate on α-aminonitriles and further reduction. Although reduction with sodium cyanoborohydride afforded a mixture of cis and trans isomers 6a-e with moderate to good stereoselectivity, reduction with sodium in liquid ammonia gave the trans isomers 8a-e with complete stereoselectivity. Acidic hydrolysis of the urea gave 4-amino-pyrrolidinones, which can be precursors to β,γ-diaminoacids or 3-aminopyrrolidines.

Asymmetric hydrogenation of N-sulfonylated-α-dehydroamino acids: Toward the synthesis of an anthrax lethal factor inhibitor

(Chemical Equation Presented) A novel and highly enantioselective Ru-catalyzed hydrogenation of N-sulfonylated-α-dehydroamino acids has been discovered and demonstrated in the synthesis of an anthrax lethal factor inhibitor (LFI). Herein, this methodology is used to prepare N-sulfonylated amino acids in up to 98% ee. This unprecedented hydrogenation uses a chiral Ru catalyst rather than Rh as typical for acylated dehydroamino acids and esters, and this work reports the first asymmetric hydrogenation of a tetrasubstituted dehydroamino acid derivative using a Ru catalyst.

Highly selective deprotection of tert-butyl esters using ytterbium triflate as a catalyst under mild conditions

Ytterbium triflate catalyses the deprotection of tert-butyl esters selectively in the presence of other esters under mild conditions in almost quantitative yields. The reactions are carried out in nitromethane (45°-50°C) using 5 mole percent of the catalyst.

A novel concept in combinatorial chemistry in solution with the advantages of solid-phase synthesis: Formation of N-betaines by multicomponent domino reactions

Advantages of solid-phase and liquid-phase synthesis are combined in a new concept of combinatorial chemistry: a domino sequence comprising Knoevenagel and hetero-Diels-Alder reactions, with subsequent hydrogenation starting from protected aminoaldehydes, 1.3-dicarbonyl compounds, and enol ethers leads to N-heterocycles of high diversity with a betaine structure, which are isolated in highly pure form by precipitation with diethyl ether (see scheme), Cbz = benzylocycarbonyl, Bn = benzyl.

New facile alkoxycarbonylating agent, alkyl pyrazole-1-carboxylates. The preparation and the utilities

Alkyl pyrazole-1-carboxylates (2), which were readily prepared from alkyl chloroformate or carbazate in good yields, were provided as the new facile alkoxycarbonylating agents toward the Grignard reagents for the synthesis of one carbon higher carboxylic esters. Also amines were alkoxycarbonylated by 2 to produce the corresponding urethanes even in an aqueous medium. Benzyl 3,5-dimethylpyrazole-1-carboxylate (2d) could be utilized for the Cbz-protection of amino acids and esters in good yield without any racemization.

Synthesis of Racemic α-Amino Carboxamides via Lewis Acid-Mediated Reactions of α-Methoxyglycinamide Derivatives with Allylsilanes: Enzymatic Resolution to Optically Active α-Amino Acids

A short and expedient synthetic route to optically active, saturated and γ,δ-unsaturated α-amino acids is reported.The key step is a BF3*Et2O-mediated reaction of allylsilanes with N-(alkoxycarbonyl)-α-methoxyglycinamides 11-15, leading to the corresponding γ,δ-unsaturated α-aminocarboxamides.The genuine SN1-character of this process with iminium ion 6 as intermediate is proven in the case of the glycine ester 10.Thus, reaction of enzymatically resolved 10 with ?-nucleophiles leads to racemic products.The most useful iminium precursors are the N-methoxyamides 12-14 providing good yields of coupling products.The most convenient N-protective group is the allyloxycarbonyl group.Deprotection proceeds via a Pd(O)-catalyzed transprotection to the corresponding BOC-protected analogues.Four examples of the enzymatic resolution of α-amino carboxamides, by using an L-specific aminopeptidase from Pseudomonas putida, are described in detail.Most notably, secondary N-methoxyamides are good substrates for the enzyme to provide the desired α-amino acids in high optical purity.

Composition containing a penem or carbapenem antibiotic and the use of the same

Administration of an N-acylated amino acid in association with a penem or carbapenem antibiotic relieves or eliminates the renal problems associated with administration of the antibiotic alone. The amino acid derivative and antibiotic may be formulated together as a composition or administered separately, either simultaneously or sequentially.

Composition containing a penem or carbapenem antibiotic

Administration of an N-acylated amino acid in association with a penem or carbapenem antibiotic relieves or eliminates the renal problems associated with administration of the antibiotic alone. The amino acid derivative and antibiotic may be formulated together as a composition or administered separately, either simultaneously or sequentially. The composition may be prepared by simple mixing.

DIISOPROPYLETHYLAMINE ELIMINATES DIPEPTIDE FORMATION DURING THE ACYLATION OF AMINO ACIDS USING BENZOYL CHLORIDE AND SOME ALKYL CHLOROFORMATES

Acylation of amino acids using benzoyl chloride in aqueous alkali leads to benzoylamino acids containing one percent of benzoyldipeptide.Use of diisopropylethylamine instead of sodium hydroxide as base eliminates the side reaction responsible for the contaminant.Ethoxycarbonylamino acids are advantageously prepared in the same manner using ethyl chloroformate or diethyl dicarbonate.The latter gives rise to some N-substituted dipeptide when used in aqueous alkali.The method is unsatisfactory for the benzyloxycarbonylation of amino acids.Use of 9-fluorenylmethyl chloroformate and diisopropylethylamine gives the pure derivative of leucine in moderate yield.