benzyl (1R,2S)-1-(3,5-bis(trifluoromethyl)phenyl)-1-hydroxypropan-2-ylcarbamate

Base Information

• Chemical Name: benzyl (1R,2S)-1-(3,5-bis(trifluoromethyl)phenyl)-1-hydroxypropan-2-ylcarbamate
• CAS No.: 877384-16-2
• Molecular Formula: C19H17F6NO3
• Molecular Weight: 421.339
• DSSTox Substance ID: DTXSID50470678
• Nikkaji Number: J2.280.139B
• Wikidata: Q72447359
• Mol file: 877384-16-2.mol

Synonyms:877384-16-2;benzyl (1R,2S)-1-(3,5-bis(trifluoromethyl)phenyl)-1-hydroxypropan-2-ylcarbamate;Benzyl ((1R,2S)-1-(3,5-bis(trifluoromethyl)phenyl)-1-hydroxypropan-2-yl)carbamate;benzyl N-[(1R,2S)-1-[3,5-bis(trifluoromethyl)phenyl]-1-hydroxypropan-2-yl]carbamate;Benzyl {(1R,2S)-1-[3,5-bis(trifluoromethyl)phenyl]-1-hydroxypropan-2-yl}carbamate;SCHEMBL13394496;DTXSID50470678;AWBAPOAGBOTVOQ-ZBEGNZNMSA-N;Benzyl ((1R,2S)-1-(3,5-bis(trifluoromethyl)-phenyl)-1-hydroxypropan-2-yl)carbamate;AMY36649;BCP18687;AKOS016005660;C90998;benzyl(1R,2S)-1-(3,5-bis(trifluoromethyl)phenyl)-1-hydroxypropan-2-ylcarbamate

Chemical Property of benzyl (1R,2S)-1-(3,5-bis(trifluoromethyl)phenyl)-1-hydroxypropan-2-ylcarbamate

Chemical Property:

• PSA: 58.56000
• Density: 1.357
• LogP: 5.46340
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 421.11126238
• Heavy Atom Count: 29
• Complexity: 511

Purity/Quality:

98%min ^*data from raw suppliers

Benzyl ((1R,2S)-1-(3,5-bis(trifluoromethyl)-phenyl)-1-hydroxypropan-2-yl)carbamate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C[C@@H]([C@@H](C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)O)NC(=O)OCC2=CC=CC=C2

Technology Process of benzyl (1R,2S)-1-(3,5-bis(trifluoromethyl)phenyl)-1-hydroxypropan-2-ylcarbamate

There total 5 articles about benzyl (1R,2S)-1-(3,5-bis(trifluoromethyl)phenyl)-1-hydroxypropan-2-ylcarbamate 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: 99.0%

benzyl {(1S)-2-[3,5-bis(trifluoromethyl)phenyl]-1-methyl-2-oxoethyl}carbamate (871917-79-2,1363382-26-6) → benzyl (1S,2R)-2-(3,5-bis(trifluoromethyl)phenyl)-2-hydroxy-1-methylethylcarbamate (877384-16-2)

Guidance literature:

With aluminum isopropoxide; In isopropyl alcohol; toluene; at 50 ℃; for 15h;

Reference yield: 97.0%

benzyl {(1S)-2-[3,5-bis(trifluoromethyl)phenyl]-1-methyl-2-oxoethyl}carbamate (871917-79-2,1363382-26-6) → (1S,2S)-1-(3',5'-bis(trifluoromethyl)phenyl)-2-benzyloxycarbonylamino-1-propanol + benzyl (1S,2R)-2-(3,5-bis(trifluoromethyl)phenyl)-2-hydroxy-1-methylethylcarbamate (877384-16-2)

Guidance literature:

With aluminum isopropoxide; isopropyl alcohol; In toluene; at 50 ℃; for 15h;

DOI:10.1021/jo052121t

Reference yield:

(S)-benzyl (1-(N,O-dimethylhydroxylamine)-1-oxopropan-2-yl)carbamate (114744-83-1,688763-83-9) → benzyl (1S,2R)-2-(3,5-bis(trifluoromethyl)phenyl)-2-hydroxy-1-methylethylcarbamate (877384-16-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: isopropylmagnesium chloride / tetrahydrofuran / 0.25 h / -15 °C / Inert atmosphere

1.2: -15 - 25 °C / Inert atmosphere

2.1: Dimethylphenylsilane; trifluoroacetic acid / 5 h / 0 °C / Inert atmosphere

With Dimethylphenylsilane; isopropylmagnesium chloride; trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1021/jm200484c

upstream raw materials:

benzyl {(1S)-2-[3,5-bis(trifluoromethyl)phenyl]-1-methyl-2-oxoethyl}carbamate

(S)-benzyl (1-(N,O-dimethylhydroxylamine)-1-oxopropan-2-yl)carbamate

3,6-bis(trifluoromethyl)bromobenzene

Downstream raw materials:

(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one

(1R,2S)-1-[3,5-bis(trifluoromethyl)phenyl]-2-[({2-[4-fluoro-2-methoxy-5-(propan-2-yl)phenyl]-5-(trifluoromethyl)phenyl}methyl)amino]propan-1-ol

anacetrapib

(1R,2S)-1-[3,5-bis(trifluoromethyl)phenyl]-2-[(E)-({2-[4-fluoro-2-methoxy-5-(propan-2-yl)phenyl]-5-(trifluoromethyl)phenyl}methylidene)amino]propan-1-ol

Refernces

• 1、 -. "Method for preparing arene beta-amino alcohol of optical voidness". Paragraph 0187; 0188; 0189. . Retrieved 2016/10/08.
• 2、 -. "PROCESS FOR PREPARATION OF ANACETRAPIB AND INTERMEDIATES THEREOF". Page/Page column 22; 23. . Retrieved 2014/08/06.