(R,R)-(-)-PSEUDOEPHEDRINE GLYCINAMIDE

Base Information

• Chemical Name: (R,R)-(-)-PSEUDOEPHEDRINE GLYCINAMIDE
• CAS No.: 170115-98-7
• Molecular Formula: C12H18 N2 O2
• Molecular Weight: 222.287
• Mol file: 170115-98-7.mol

Synonyms:Acetamide,2-amino-N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methyl-, [R-(R*,R*)]-

Chemical Property of (R,R)-(-)-PSEUDOEPHEDRINE GLYCINAMIDE

Chemical Property:

• Boiling Point: 397.8±42.0 °C(Predicted)
• PKA: 13.71±0.20(Predicted)
• PSA: 66.56000
• Density: 1.140±0.06 g/cm3(Predicted)
• LogP: 1.22590

Purity/Quality:

98%min ^*data from raw suppliers

(R,R)-(-)-PseudoephedrineGlycinamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (R,R)-(-)-Pseudoephedrine Glycinamide is a building block used as a reactant in the synthesis of macrocyclic trypanosomal cysteine protease inhibitors and in the synthesis of α-amino acids.

Technology Process of (R,R)-(-)-PSEUDOEPHEDRINE GLYCINAMIDE

There total 5 articles about (R,R)-(-)-PSEUDOEPHEDRINE GLYCINAMIDE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

(1R,2R)-pseudoephedrine (321-97-1,7009-81-6,90-83-5,6912-63-6) + glycine ethyl ester hydrochloride (5680-79-5,883886-67-7) → 2-amino-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N-methylacetamide (170115-98-7)

Guidance literature:

(1R,2R)-pseudoephedrine; glycine ethyl ester hydrochloride; With lithium tert-butoxide; In tetrahydrofuran; at 23 ℃; for 2h;

With water; In tetrahydrofuran;

Reference yield: 70.0%

BOC-glycine (4530-20-5) + (1R,2R)-pseudoephedrine (321-97-1,7009-81-6,90-83-5,6912-63-6) + pivaloyl chloride (3282-30-2) → 2-amino-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N-methylacetamide (170115-98-7)

Guidance literature:

BOC-glycine; pivaloyl chloride; With triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

(1R,2R)-pseudoephedrine; With triethylamine; In dichloromethane; at 0 ℃; for 0.666667h;

With hydrogenchloride; In methanol; at 0 ℃; for 3h; Further stages.;

DOI:10.1002/ejoc.200300400

Reference yield: 67.0%

(1R,2R)-pseudoephedrine (321-97-1,7009-81-6,90-83-5,6912-63-6) + methoxycarbonylmethylamine (616-34-2) → 2-amino-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N-methylacetamide (170115-98-7)

Guidance literature:

(1R,2R)-pseudoephedrine; With lithium chloride; In tetrahydrofuran; for 0.25h; Inert atmosphere; Cooling with ice;

With lithium methanolate; In tetrahydrofuran; at 0 ℃; for 0.166667h; Inert atmosphere;

methoxycarbonylmethylamine; In tetrahydrofuran; at 0 ℃; for 8h; Reagent/catalyst; Inert atmosphere;

DOI:10.15227/orgsyn.076.0057

upstream raw materials:

BOC-glycine

(1R,2R)-pseudoephedrine

methoxycarbonylmethylamine

2-amino-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylacetamide

Downstream raw materials:

<1R(S),2R>-N-(2-hydroxy-1-methyl-2-phenethyl)-2-amino-N-methyl-4-pentenamide

Refernces

• 1、 -. "SULFONAMIDE COMPOUNDS". Page/Page column 19-20. . Retrieved 2010/10/20.
• 2、 -. "Aspartyl protease inhibitors". Page 43. . Retrieved 2010/02/07.