19525-87-2

Basic information

• Product Name: O-BENZYL-L-SERINE METHYL ESTER HYDROCHLORIDE
• Synonyms: O-BENZYL-L-SERINE METHYL ESTER HYDROCHLORIDE;METHYL O-BENZYL-L-SERINATE HYDROCHLORIDE;H-SER(BZL)-OME HCL;Benzylserinemethylesterhydrochloride;o-benzyl-l-serinemethylesterHCl;Methyl O-Benzyl-L-serinate Hydrochloride H-Ser(Bzl)-OMe.HCl;O-Benzyl-L-serine Methyl Ester Hydrochloride;(S)-Methyl 2-aMino-3-(benzyloxy)propanoate hydrochloride
• CAS NO: 19525-87-2
• Molecular Formula: C₁₁H₁₅NO₃*ClH
• Molecular Weight: 245.7
• EINECS: 1533716-785-6
• Product Categories: Amino Acid Methyl Esters;Amino Acids;Amino Acids (C-Protected);Biochemistry
• Mol File: 19525-87-2.mol

Chemical Properties

• Melting Point: 164-166 °C
• Boiling Point: 330.2°C at 760 mmHg
• Flash Point: 146.7°C
• Appearance: /
• Density: 1.126g/cm³
• Vapor Pressure: 0.000169mmHg at 25°C
• Refractive Index: 5 ° (C=1, MeOH)
• Storage Temp.: Store at 0°C
• Water Solubility: almost transparency
• CAS DataBase Reference: O-BENZYL-L-SERINE METHYL ESTER HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: O-BENZYL-L-SERINE METHYL ESTER HYDROCHLORIDE(19525-87-2)
• EPA Substance Registry System: O-BENZYL-L-SERINE METHYL ESTER HYDROCHLORIDE(19525-87-2)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 19525-87-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
O-Benzyl-L-serine Methyl Ester Hydrochloride is used as a reactant for the synthesis of ureidopeptides and peptidyl ureas. These compounds are important in the development of novel drugs with potential therapeutic applications. The use of this reactant allows for the creation of diverse and complex molecular structures, which can be tailored to target specific biological pathways or receptors.
In the synthesis of ureidopeptides and peptidyl ureas, O-Benzyl-L-serine Methyl Ester Hydrochloride plays a crucial role in forming the backbone of these molecules. The benzyl group provides steric hindrance and electronic effects that can influence the reactivity and selectivity of the reaction, while the methyl ester group can be used for further functionalization or as a protecting group during the synthesis process.
The applications of ureidopeptides and peptidyl ureas are vast, ranging from the development of new antibiotics to the design of potent enzyme inhibitors. These compounds can also be used as building blocks for the construction of larger peptide-based drugs or as components of drug delivery systems.

InChI:InChI=1/C11H15NO3/c1-14-11(13)10(12)8-15-7-9-5-3-2-4-6-9/h2-6,10H,7-8,12H2,1H3

Upstream product

• 67-56-1 methanol 
• 4726-96-9 O-Benzyl-L-serine 
• 76614-98-7 O-benzyl-L-serine hydrochloride 
• 23680-31-1 BOC-O-benzyl-L-serine 
• 46460-82-6 O-benzyl-L-serine methyl ester 

Downstream Products

• 40470-04-0 N-Benzyloxycarbonyl-β-benzylaspartyl-O-benzylserinmethylester 
• 445474-17-9 methyl (2S)-2-(N,N-dibenzylamino)-3-benzyloxypropanoate 
• 427882-47-1 methyl (2S)-2-(benzoylamino)-3-benzyloxypropanoate 
• 24629-06-9 N-tret-butoxycarbonyl-L-tryptophanyl-O-benzyl-L-serine methyl ester 
• 54613-92-2 Boc-Thr(Bzl)-Ser(Bzl)-OH 
• 868633-24-3 (S)-3-benzyloxy-2-[4-chloro-6-(4-pyridin-2-yl-piperazin-1-yl)-[1,3,5]triazin-2-yl-amino]propionic acid methyl ester 
• 198701-20-1 N-[[(4,5-dihydro-5-thioxo-1,3,4-thiadiazol-2-yl)amino]carbonyl]-O-(phenylmethyl)-L-serine methyl ester 
• 1060662-36-3 methyl (2S)-6-(4-nitrobenzenesulfonyl)-2-(benzyloxymethyl)-3,6-diaza-4-oxohexanoate 
• 1228178-43-5 Fmoc-Ile-Gly-ψ(NH-CO-NH)-Ser(Bzl)-OMe 
• 1428095-58-2 methyl O-benzyl-N-(3α-hydroxy-5β-cholan-24-oyl)-L-serinate 
• 67320-80-3 (S)-2-Amino-3-benzyloxy-propionamide 
• 1386995-56-7 (S)-3-(benzyloxy)-2-(4-nitrophenylsulfonamido)propanamide 
• 1313239-36-9 (S)-3-(benzyloxy)-2-(4-nitro-N-(prop-2-yn-1-yl)phenylsulfonamido)propanamide 

Relevant articles and documents

Gram-Scale Solution-Phase Synthesis of Heptapeptide Side Chain of Teixobactin 1

We report herein a scalable synthesis of linear heptapeptide side chain of the depsipeptide natural product teixobactin through solution phase. The synthesis of heptapeptide was achieved through an efficient coupling of suitably protected tripeptide and tetrapeptide comprising of three d-amino acids and four usual l-amino acid subunits.

Amino acid conjugates of lithocholic acid as antagonists of the EphA2 receptor

The Eph receptor-ephrin system is an emerging target for the development of novel antiangiogenetic agents. We recently identified lithocholic acid (LCA) as a small molecule able to block EphA2-dependent signals in cancer cells, suggesting that its (5β)-cholan-24-oic acid scaffold can be used as a template to design a new generation of improved EphA2 antagonists. Here, we report the design and synthesis of an extended set of LCA derivatives obtained by conjugation of its carboxyl group with different α-amino acids. Structure-activity relationships indicate that the presence of a lipophilic amino acid side chain is fundamental to achieve good potencies. The l-Trp derivative (20, PCM126) was the most potent antagonist of the series disrupting EphA2-ephrinA1 interaction and blocking EphA2 phosphorylation in prostate cancer cells at low μM concentrations, thus being significantly more potent than LCA. Compound 20 is among the most potent small-molecule antagonists of the EphA2 receptor.

Continuous multiple liquid-liquid separation: Diazotization of amino acids in flow

A second-generation laboratory-scale, modular liquid-liquid separation device based on computer-controlled high-pressure pumps and a high-resolution digital camera has been invented. The diazotization of amino acids to produce valuable chiral hydroxyacids is demonstrated in flow for the first time. The use of a triple-separator system in conjuction with the developed diazotization process allows the safe and efficient production and automated isolation of multigram quantities of valuable chiral hydroxyacids.

SUBSTITUTED AMINO-BENZIMIDAZOLES, MEDICAMENTS COMPRISING SAID COMPOUND, THEIR USE AND THEIR METHOD OF MANUFACTURE

The present invention relates to substituted amino-benzimidazoles of general formula (1) wherein the groups R1 to R14 and A, are defined as in the specification and claims and the use thereof for the treatment of Alzheimer's disease (AD) and similar diseases.

New efficient enantioselective synthesis of 2-oxopiperazines: a practical access to chiral 3-substituted 2-oxopiperazines

The development of efficient and stereoselective methods to produce 1,4-disubstituted-2-oxopiperazine in enantiomerically pure form, from a readily available starting material is crucial. Herein, we report a reduction modification to our previously descri

Efficient synthesis of 2,5-diketopiperazines using microwave assisted heating

In this study a general, efficient and environmentally benign solution phase synthesis of 2,5-diketopiperazines (DKPs) using microwave assisted heating in water is described. A series of 11 structurally different DKPs have been synthesized from dipeptide methyl esters. A range of common laboratory solvents have been tested as well as different reaction times and temperatures. Both classic thermal and microwave assisted heating have been investigated. Microwave assisted heating for 10 min using water as solvent proved, by far, to be the most efficient method of cyclization giving moderate to excellent yields (63-97%) of DKPs. In contrast to other published procedures, this method seems independent of the amino acid sequence.

Ultrasound accelerated synthesis of proteinogenic and α,α- dialkylamino acid ester salts

A simple and efficient sonochemical esterification of proteinogenic as well as cyclic α,α-dialkyl amino acid methyl and ethyl ester hydrochloride salts employing thionyl chloride and alcohol has been reported. All the amino acid esters made have been obtained in good yield (94-98%) as pure compounds.

Approaches to the synthesis of (2R,3S)-2-hydroxymethylpyrrolidin-3-ol (CYB-3) and its C(3) epimer: A cautionary tale

The syntheses of (2R,3S)-2-tert-butyldiphenylsilyloxymethylpyrrolidin-3-ol (TBDPS-protected CYB-3) (21) and its C(3) epimer (25) have been achieved in 9 and 8 steps respectively from D-serine. However, chiral HPLC analysis of the key β-hydroxy ester intermediates in these syntheses (17 and 18) revealed that appreciable levels of racemisation had occurred in the aldol and Claisen condensation reactions used in this synthetic sequence.

Bicyclic compounds derived from tartaric acid and α-amino acids (BTAas): Synthesis of new molecular scaffolds derived from the combination of (R,R)-tartaric acid and L-serine

The synthesis of the new N-Fmoc-protected dipeptide isoster methyl (1S,2S,5S,6R)-2exo-hydroxymethyl-7,8-dioxa-3-azabicyclo [3.2.1] octane-6 exo-carboxylate (BTS) has been achieved, starting from (R,R)-tartaric acid and O-benzyl-L-serine, in 11% overall yield after 9 steps. Interestingly, starting from the same α-amino acid, it was also possible to prepare the 2endo-substituted compound, formally derived from the combination of tartaric acid with D-serine. Each compound has a CH2OH functional group at C-2, which is very useful for greater diversification of the 7,8-dioxa-3-azabicyclo [3.2.1]octane-6-carboxylate (BTAa) dipeptide isosters. The oxidation of the C-2 carbinol group in BTS, moreover, gave rise to a novel, conformationally constrained, α-amino acid that may find application in peptidomimetic synthesis.

Convenient procedures for the synthesis of N-BOC-D-serinal acetonide from L-serine

Two straightforward synthetic routes for the preparation of enantiomerically pure N-BOC-D-serinal acetonide (enantiomer of Garner's aldehyde) starting from naturally occurring L-serine are described.