N-((2S,3S,5S)-5-Amino-3-hydroxy-1,6-diphenylhexan-2-yl)-2-(2,6-dimethylphenoxy)acetamide

Base Information

• Chemical Name: N-((2S,3S,5S)-5-Amino-3-hydroxy-1,6-diphenylhexan-2-yl)-2-(2,6-dimethylphenoxy)acetamide
• CAS No.: 192725-49-8
• Molecular Formula: C28H34N2O3
• Molecular Weight: 446.59
• UNII: S21JGQ154U
• DSSTox Substance ID: DTXSID10172868
• Nikkaji Number: J1.543.457K
• Wikidata: Q27288469
• Mol file: 192725-49-8.mol

Synonyms:192725-49-8;N-((2S,3S,5S)-5-Amino-3-hydroxy-1,6-diphenylhexan-2-yl)-2-(2,6-dimethylphenoxy)acetamide;Lopinavir phenoxyacetamide;(2S,3S,5S)-2-(2,6-DIMETHYLPHENOXYACETYL)AMINO-3-HYDROXY-5-AMINO-1,6-DIPHENYLHEXANE;N-[(1S,2S,4S)-4-AMINO-2-HYDROXY-5-PHENYL-1-(PHENYLMETHYL)PENTYL]-2-(2,6-DIMETHYLPHENOXY)ACETAMIDE;Lopinavir impurity E [EP];UNII-S21JGQ154U;S21JGQ154U;N-((1S,2S,4S)-4-Amino-1-benzyl-2-hydroxy-5-phenylpentyl)-2-(2,6-dimethylphenoxy)acetamide;Acetamide, N-((1S,2S,4S)-4-amino-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl)-2-(2,6-dimethylphenoxy)-;N-[(2S,3S,5S)-5-AMINO-3-HYDROXY-1,6-DIPHENYLHEXAN-2-YL]-2-(2,6-DIMETHYLPHENOXY)ACETAMIDE;Lopinavir impurity, lopinavir phenoxyacetamide- [USP];Acetamide, N-[(1S,2S,4S)-4-amino-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-2-(2,6-dimethylphenoxy)-;SCHEMBL672415;DTXSID10172868;LWXUXIDLCWPHIW-GSDHBNRESA-N;AKOS015909344;AC-8897;CS-O-30829;LOPINAVIR IMPURITY E [EP IMPURITY];J-012469;J-523292;Q27288469;LOPINAVIR IMPURITY, LOPINAVIR PHENOXYACETAMIDE- [USP IMPURITY];(2S, 3S, 5S) -2-(2,6-Dimethylphenoxyacetyl) amino-3-hydroxy-5-amino-1,6-diphenylhexane;(2S, 3S, 5S)-2-(2,6-Dimethylphenoxyacetyl) amino-3-hydroxy-5-amino-1,6-diphenylhexane;(2S,3S,5S) -2-(2,6-Dimethylphenoxyacetyl) amino-3-hydroxy-5-amino-1,6-diphenylhexane;N-[(1S,2S,4S)-1-Benzyl-2-hydroxy-4-amino-5-phenylpentyl]-2-(2,6-dimethylphenoxy)acetamide;N-[(1S,2S,4S)-4-amino-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-2-(2,6-dimethylphenoxy) Acetamide

Chemical Property of N-((2S,3S,5S)-5-Amino-3-hydroxy-1,6-diphenylhexan-2-yl)-2-(2,6-dimethylphenoxy)acetamide

Chemical Property:

• Appearance/Colour: Off-white solid
• Melting Point: 124-126 °C
• PSA: 84.58000
• LogP: 4.82190
• Storage Temp.: Refrigerator
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 446.25694295
• Heavy Atom Count: 33
• Complexity: 549

Purity/Quality:

99% ^*data from raw suppliers

(2S,3S,5S)-2-(2,6-Dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-1,6-diphenylhexane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=CC=C1)C)OCC(=O)NC(CC2=CC=CC=C2)C(CC(CC3=CC=CC=C3)N)O
• Isomeric SMILES: CC1=C(C(=CC=C1)C)OCC(=O)N[C@@H](CC2=CC=CC=C2)[C@H](C[C@H](CC3=CC=CC=C3)N)O
• Uses: (2S,3S,5S)-2-(2,6-Dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-1,6-diphenylhexane (cas# 192725-49-8) is a compound useful in organic synthesis.

Technology Process of N-((2S,3S,5S)-5-Amino-3-hydroxy-1,6-diphenylhexan-2-yl)-2-(2,6-dimethylphenoxy)acetamide

There total 10 articles about N-((2S,3S,5S)-5-Amino-3-hydroxy-1,6-diphenylhexan-2-yl)-2-(2,6-dimethylphenoxy)acetamide 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: 100.0%

(2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane (192725-45-4) → (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-1,6-diphenylhexane (192725-49-8)

Guidance literature:

Reference yield:

CF3 CO2 H + dichloromethane (75-09-2) + (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane (192725-45-4) → (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-1,6-diphenylhexane (192725-49-8)

Guidance literature:

With hydrogenchloride; sodium hydrogencarbonate; In diethyl ether; water;

Reference yield:

(2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane (144163-85-9) → (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-1,6-diphenylhexane (192725-49-8)

Guidance literature:

Multi-step reaction with 2 steps

1: EDC

2: trifluoroacetic acid

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid;

DOI:10.1016/S0960-894X(02)00643-1

upstream raw materials:

(2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane

(2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane

(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane

Downstream raw materials:

lopinavir

C₇₄H₉₆N₆O₁₅

(S)-N-{(1S,3S,4S)-1-Benzyl-4-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-hydroxy-5-phenyl-pentyl}-2-(4-hydroxy-2-oxo-tetrahydro-pyrimidin-1-yl)-3-methyl-butyramide

Refernces

• 1、 -. "Preparation method of lopinavir". Paragraph 0004; 0006; 0008-0009. . Retrieved 2021/10/05.
• 2、 -. "A PROCESS FOR THE SYNTHESIS OF 2-AMINO-5-PROTECTED AMINO-3-HYDROXY-1, 6-DIPHENYLHEXANE OR A SALT THEREOF - AN INTERMEDIATE FOR ANTIVIRAL DRUGS". Page/Page column 21-22. . Retrieved 2008/06/13.