170115-96-5

Basic information

• Product Name: (S,S)-(+)-PSEUDOEPHEDRINE GLYCINAMIDE
• Synonyms: (+)-2-Amino-N-[(1S,2S)-(2-hydroxy-1-methyl-2-phenyl)ethyl]-N-methylacetamide, 97%;(1S, 2S)-(+)-Pseudoephedrine glycinamide, 2-Amino-N-[(2-hydroxy-1-methyl-2-phenyl)ethyl]-N-methylacetamide;Zinc04202572;[S-(R*,*)]-(+)-2-AMINO-N-(2-HYDROXY-1-METHYL-2-PHENYLETHYL)-
• CAS NO: 170115-96-5
• Molecular Formula: C₁₂H₁₈N₂O₂
• Molecular Weight: 222.28
• Mol File: 170115-96-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 76-80 °C(lit.)
• Boiling Point: 397.8°Cat760mmHg
• Flash Point: 194.4°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 4.84E-07mmHg at 25°C
• Refractive Index: 1.56
• PKA: 13.71±0.20(Predicted)
• CAS DataBase Reference: (S,S)-(+)-PSEUDOEPHEDRINE GLYCINAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (S,S)-(+)-PSEUDOEPHEDRINE GLYCINAMIDE(170115-96-5)
• EPA Substance Registry System: (S,S)-(+)-PSEUDOEPHEDRINE GLYCINAMIDE(170115-96-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 170115-96-5(Hazardous Substances Data)

Usage

Description

(S,S)-(+)-Pseudoephedrine Glycinamide is an organic compound that serves as a crucial intermediate in the synthesis of various α-amino acids. It is characterized by its chiral structure, with both stereocenters having the S configuration, and exhibits a positive optical rotation. (S,S)-(+)-PSEUDOEPHEDRINE GLYCINAMIDE plays a significant role in the pharmaceutical and chemical industries due to its ability to facilitate the production of essential α-amino acids.

Uses

Used in Pharmaceutical Industry:
(S,S)-(+)-Pseudoephedrine Glycinamide is used as a precursor for the synthesis of α-amino acids, which are vital building blocks for various pharmaceutical compounds. These amino acids are essential for the development of new drugs, particularly those targeting specific medical conditions or diseases.
Used in Chemical Industry:
In the chemical industry, (S,S)-(+)-Pseudoephedrine Glycinamide is utilized as a key intermediate in the production of various specialty chemicals and materials. Its unique chiral structure allows for the creation of enantiomerically pure compounds, which are crucial in various applications, such as chiral catalysts and ligands for asymmetric synthesis.
Used in Research and Development:
(S,S)-(+)-Pseudoephedrine Glycinamide is also employed in research and development settings, where it is used to study the properties and reactivity of chiral compounds. This knowledge can be applied to the design and synthesis of novel molecules with specific biological activities or improved pharmaceutical properties.

InChI:InChI=1/C12H18N2O2/c1-9(14(2)11(15)8-13)12(16)10-6-4-3-5-7-10/h3-7,9,12,16H,8,13H2,1-2H3/t9-,12+/m0/s1

Upstream product

• 4530-20-5 BOC-glycine 
• 90-82-4 pseudoephedrine 
• 616-34-2 methoxycarbonylmethylamine 
• 161203-15-2 N-Boc-glycine-pivalic acid mixed anhydride 
• 185508-77-4 {[((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-methyl-carbamoyl]-methyl}-carbamic acid tert-butyl ester 
• 52289-93-7 o-Methoxybenzyl bromide 
• 185508-75-2 (S,S)-pseudoephedrine N-methylglycinamide 
• 170642-24-7 (R)-2-Amino-4-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide 
• 170642-33-8 (S,S)-pseudoephedrine N-methyl-D-phenylalaninamide 
• 170642-21-4 (S,S)-pseudoephedrine D-2-aminobutyramide 
• 170642-22-5 (R)-2-Amino-3-cyclopropyl-N-((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-propionamide 
• 170899-07-7 (S,S)-pseudoephedrine D-phenylalaninamide 

Downstream Products

• 170642-32-7 (S,S)-pseudoephedrine D-pipecolinamide 
• 170642-24-7 (R)-2-Amino-4-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide 
• 90-82-4 pseudoephedrine 
• 219819-76-8 (R)-2-tert-Butoxycarbonylamino-hex-5-enoic acid 
• 89483-08-9 (R)-2-((tert-butoxycarbonyl)amino)-3-cyclopropylpropanoic acid 
• 121786-39-8 (R)-2-amino-3-cyclopropylpropanoic acid 
• 103067-78-3 (2R)-2-amino-5-hexenoic acid 
• 170642-22-5 (R)-2-Amino-3-cyclopropyl-N-((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-propionamide 
• 170642-26-9 D-N-tert-butoxycarbonyl-2-methoxyphenylalanine 
• 170642-31-6 (2R)-2-amino-3-(2-methoxyphenyl)propanoic acid 
• 170642-25-8 (R)-2-Amino-N-((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-3-(2-methoxy-phenyl)-N-methyl-propionamide 
• 170899-07-7 (S,S)-pseudoephedrine D-phenylalaninamide 
• 170642-21-4 (S,S)-pseudoephedrine D-2-aminobutyramide 
• 170642-23-6 (S,S)-pseudoephedrine D-allylglycinamide 

Relevant articles and documents

A One-Step Synthesis of Pseudoephedrine Glycinamide, a Versatile Precursor for the Synthesis of a α-Amino Acids

Both enantiomers of pseudoephedrine glycinamide were synthesized by either of two procedures: (1) a standard two-step coupling of N-Boc-Gly with pseudoephedrine followed by deprotection, or (2) a more economical one-step coupling reaction of Gly-OMe with pseudoephedrine mediated by LiCl and base.

Highly practical methodology for the synthesis of D- and L-α-amino acids, N-protected α-amino acids, and N-methyl-α-amino acids

Full details are provided for an exceedingly practical method to synthesize D- and L-α-amino acids, N-protected α-amino acids, and N-methyl-α-amino acids, employing as a key step the asymmetric alkylation of pseudoephedrine glycinamide (1) or pseudoephedrine sarcosinamide (2). Practical procedures for the synthesis of 1 and 2 from pseudoephedrine and glycine methyl ester or sarcosine methyl ester, respectively, are presented. Optimum protocols for the enolization and subsequent alkylation of 1 and 2 are described. Alkylation reactions of 1 and 2 are found to be quite efficient with a wide range of alkyl halide substrates, and the products are formed with high diastereoselectivity. The products of these alkylation reactions are hydrolyzed efficiently and with little to no racemization simply by heating in water or water-dioxane mixtures. This protocol provides an exceedingly practical method for the preparation of salt-free α-amino acids of high enantiomeric purity. Alternatively, the alkylation products may be hydrolyzed in high yield and with little to no racemization by heating with aqueous sodium hydroxide. The alkaline hydrolyzate can then be treated with an acylating reagent to provide directly highly enantiomerically enriched N-protected derivatives such as N-Boc and N-Fmoc. Key features necessary for the successful execution of these experimental procedures are identified.