1253790-58-7

Basic information

• Product Name: Boc-D-Serine BenzylaMide
• Synonyms: Lacosamide Impurity 18;tert-Butyl (R)-(1-(benzylamino)-3-hydroxy-1-oxopropan-2-yl)carbamate;tert-butyl N-[(2R)-1-(benzylamino)-3-hydroxy-1-oxopropan-2-yl]carbamate;Carbamic acid, N-[(1R)-1-(hydroxymethyl)-2-oxo-2-[(phenylmethyl)amino]ethyl]-, 1,1-dimethylethyl ester
• CAS NO: 1253790-58-7
• Molecular Formula: C₁₅H₂₂N₂O₄
• Molecular Weight: 294.34618
• Mol File: 1253790-58-7.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 532.9±50.0 °C(Predicted)
• Appearance: /
• Density: 1.159±0.06 g/cm3(Predicted)
• PKA: 10.62±0.46(Predicted)
• CAS DataBase Reference: Boc-D-Serine BenzylaMide(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-D-Serine BenzylaMide(1253790-58-7)
• EPA Substance Registry System: Boc-D-Serine BenzylaMide(1253790-58-7)

Safety Data

• Hazardous Substances Data: 1253790-58-7(Hazardous Substances Data)

Usage

General Description

Boc-D-Serine Benzylamide is a chemical compound used in biochemical research and pharmaceutical development. It is a derivative of D-Serine, an amino acid that acts as a neurotransmitter in the central nervous system. The compound is commonly used as a building block in the synthesis of peptides and pharmaceuticals, and its properties make it useful for studying the structure and function of proteins. Boc-D-Serine Benzylamide is known for its stability and compatibility with a wide range of chemical reactions, making it a valuable tool for researchers and drug developers. It is typically used in controlled laboratory settings under strict safety guidelines.

Upstream product

• 3262-72-4 (R)-N-tert-butoxycarbonyl serine 
• 100-46-9 benzylamine 
• 86123-95-7 (R)-2-((tert-butoxycarbonyl)amino)-3-methoxypropionic acid 
• 1357171-70-0 (2S)-N-benzyl-2-bromo-3-hydroxypropanamide 
• 1357171-71-1 (2R)-2-azido-N-benzyl-3-hydroxypropanamide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 175481-39-7 (2R)-2-amino-3-hydroxy-N-(phenylmethyl)propanamide 
• 1263296-25-8 tert-butyl {(1R)-2-(benzylamino)-2-oxo-1-[(tetrahydro-2H-pyran-2-yloxy)methyl]ethyl}carbamate 

Downstream Products

• 880468-89-3 tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate 
• 175481-36-4 lacosamide 
• 196601-69-1 (R)-2-amino-N-benzyl-3-methoxypropanamide 
• 175481-38-6 Desmethyllacosamide 
• 175481-39-7 (2R)-2-amino-3-hydroxy-N-(phenylmethyl)propanamide 
• 1322062-75-8 (2R)-2-amino-N-benzyl-3-hydroxypropanamide hydrochloride 
• 1322062-76-9 (R)-2-amino-N-benzyl-3-methoxypropionamide hydrochloride 
• 1320360-92-6 (R)-N-benzyl-2-(ethoxycarbonylamino)-3-methoxypropionamide 
• 1320360-91-5 (R)-N-benzyl-2-(ethoxycarbonylamino)-3-hydroxypropionamide 

Relevant articles and documents

Improved Synthesis and Impurity Identification of (R)-Lacosamide

An improved synthesis of Lacosamide 1 with high purity has been developed. Critical parameters of each step were identified as well as the impurities generated. Moreover, a creative method to improve chiral purity and stability of the key intermediate (R)-2-amino-N-benzyl-3-methoxypropionamide 10 by forming salt with an achiral acid (phosphoric acid) was discovered to ensure the chiral purity of (R)-Lacosamide. Phosphoric acid was further developed for the deprotection of the Boc group.

Improved preparation method of modified lacosamide

The invention discloses an improved preparation method of modified lacosamide, which is simple to operate, high in chiral purity and low in cost. According to the improved preparation method, in step 1, amidation is carried out on amino by utilizing di-tert butyl dicarbonate (Boc for short), wherein conditions are moderate and the chiral purity is high and at least reaches 90 percent or more; in step 4, high-selectivity dimethyl sulfate is used as a methylation reagent; the cost is low and the conditions are moderate; the methylation yield is high and the improved preparation method is more suitable for large-scale application. The improved preparation method has the most important innovation points that the Boc is used as an N-protection agent and a Boc protecting group can be simply and conveniently removed by adding acid and a hydrogenation removal means does not need to be used. Secondly, the low-price dimethyl sulfate is used for carrying out methylation and the conditions are moderate; the methylation yield is high and the improved preparation method is more suitable for large-scale application.

A raco amide analogs and its preparation method

The invention discloses a Lacosamide analogue and a preparation method thereof, and provides the Lacosamide analogue shown in a formula (I). The invention further provides the preparation method of the Lacosamide analogue shown in the formula (I), including: subjecting a compound shown in a formula (II) and methylated solution in two-phase solvent of organic solvent and water, and in the presence of alkali and phase transfer catalyst to substitution reaction for 20 to 100 hours, so as to obtain the compound shown in the formula (I). The Lacosamide analogue shown in the formula (I) is a necessity for quality control of Lacosamide; the preparation method can be used for efficiently synthesizing the analogue.