(S)-5-Chloro-alpha-(cyclopropylacetenyl)-2-[((4-methoxyphenyl)methyl)amino]-alpha-(trifluoromethyl)benzenemethanol

Base Information

• Chemical Name: (S)-5-Chloro-alpha-(cyclopropylacetenyl)-2-[((4-methoxyphenyl)methyl)amino]-alpha-(trifluoromethyl)benzenemethanol
• CAS No.: 173676-60-3
• Molecular Formula: C21H19 Cl F3 N O2
• Molecular Weight: 409.836
• UNII: RUK6A4RQ7D
• DSSTox Substance ID: DTXSID501109058
• Nikkaji Number: J1.067.508A
• ChEMBL ID: CHEMBL3344475
• Mol file: 173676-60-3.mol

Synonyms:173676-60-3;RUK6A4RQ7D;SD-572;UNII-RUK6A4RQ7D;(2S)-2-[5-Chloro-2-[(4-methoxyphenyl)methylamino]phenyl]-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol;(S)-5-Chloro-alpha-(cyclopropylacetenyl)-2-[((4-methoxyphenyl)methyl)amino]-alpha-(trifluoromethyl)benzenemethanol;(2S)-2-(5-Chloro-2-((4-methoxyphenyl)methylamino)phenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol;(S)-5-Chloro-alpha-(cyclopropylethynyl)-2-[[(4-methoxyphenyl)methyl]amino]-alpha-(trifluoromethyl)benzenemet;(alphaS)-5-Chloro-alpha-(2-cyclopropylethynyl)-2-(((4-methoxyphenyl)methyl)amino)-alpha-(trifluoromethyl)benzenemethanol;Benzenemethanol, 5-chloro-alpha-(2-cyclopropylethynyl)-2-(((4-methoxyphenyl)methyl)amino)-alpha-(trifluoromethyl)-, (alphaS)-;(alphaS)-5-Chloro-alpha-(2-cyclopropylethynyl)-2-[[(4-methoxyphenyl)methyl]amino]-alpha-(trifluoromethyl)benzenemethanol;SCHEMBL6438280;CHEMBL3344475;DTXSID501109058;A899425;(.ALPHA.S)-5-CHLORO-.ALPHA.-(2-CYCLOPROPYLETHYNYL)-2-(((4-METHOXYPHENYL)METHYL)AMINO)-.ALPHA.-(TRIFLUOROMETHYL)BENZENEMETHANOL;(S)-5-Chloro-?-(2-cyclopropylethynyl)-2-[[(4-methoxyphenyl)methyl]amino]-?-(trifluoro-methyl)benzenemethanol;(S)-5-Chloro-alpha-(2-cyclopropylethynyl)-2-[[(4-methoxyphenyl)methyl]amino]-alpha-(trifluoro-methyl)benzenemethanol;2-{5-Chloro-2-[(4-methoxybenzyl)amino]phenyl}-4-cyclopropyl- 1,1,1-trifluorobut-3-yn-2-ol;BENZENEMETHANOL, 5-CHLORO-.ALPHA.-(2-CYCLOPROPYLETHYNYL)-2-(((4-METHOXYPHENYL)METHYL)AMINO)-.ALPHA.-(TRIFLUOROMETHYL)-, (.ALPHA.S)-

Chemical Property of (S)-5-Chloro-alpha-(cyclopropylacetenyl)-2-[((4-methoxyphenyl)methyl)amino]-alpha-(trifluoromethyl)benzenemethanol

Chemical Property:

• Appearance/Colour: White or light yellow crystalline powder
• Melting Point: 137-141ºC
• PSA: 41.49000
• LogP: 5.19700
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Methanol
• XLogP3: 6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 409.1056410
• Heavy Atom Count: 28
• Complexity: 589

Purity/Quality:

99% ^*data from raw suppliers

(S)-5-Chloro-α-(cyclopropylethynyl)-2-[[(4-methoxyphenyl)methyl]amino]-α-(trifluoromethyl)benzenemethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)CNC2=C(C=C(C=C2)Cl)C(C#CC3CC3)(C(F)(F)F)O
• Isomeric SMILES: COC1=CC=C(C=C1)CNC2=C(C=C(C=C2)Cl)[C@@](C#CC3CC3)(C(F)(F)F)O
• Uses: (S)-5-Chloro-α-(cyclopropylethynyl)-2-[[(4-methoxyphenyl)methyl]amino]-α-(trifluoromethyl)benzenemethanol is the S enantiomer of rac-5-Chloro-α-(cyclopropylethynyl)-2-[[(4-methoxyphenyl)methyl]amino]-α-(trifluoromethyl)benzenemethanol (C365145). (S)-5-Chloro-α-(cyclopropylethynyl)-2-[[(4-methoxyphenyl)methyl]amino]-α-(trifluoromethyl)benzenemethanol is also an impurity of Efavirenz (E425000), an HIV-1 reverse transcriptase inhibitor.

Technology Process of (S)-5-Chloro-alpha-(cyclopropylacetenyl)-2-[((4-methoxyphenyl)methyl)amino]-alpha-(trifluoromethyl)benzenemethanol

There total 7 articles about (S)-5-Chloro-alpha-(cyclopropylacetenyl)-2-[((4-methoxyphenyl)methyl)amino]-alpha-(trifluoromethyl)benzenemethanol 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: 97.8%

Cyclopropylacetylene (6746-94-7) + 1-{5-chloro-2-[(4-methoxybenzyl)amino]phenyl}-2,2,2-trifluoroethan-1-one (173676-54-5) → (S)-5-chloro-α-(cyclopropylethynyl)-2-<<(4-methoxyphenyl)methyl>amino>-α-(trifluoromethyl)benzenemethanol (173676-60-3)

Guidance literature:

Cyclopropylacetylene; With n-hexyllithium; (1R,2S)-1-phenyl-2-(1-pyrrolidinyl)-1-propanol; In tetrahydrofuran; hexane; toluene; at -20 ℃; Inert atmosphere;

1-{5-chloro-2-[(4-methoxybenzyl)amino]phenyl}-2,2,2-trifluoroethan-1-one; With n-hexyllithium; In tetrahydrofuran; hexane; toluene; at -43 ℃; enantioselective reaction; Inert atmosphere;

DOI:10.1021/op025595s

Reference yield: 95.0%

1-{5-chloro-2-[(4-methoxybenzyl)amino]phenyl}-2,2,2-trifluoroethan-1-one (173676-54-5) + cyclopropyl acetylenyllithium (201218-09-9) → (S)-5-chloro-α-(cyclopropylethynyl)-2-<<(4-methoxyphenyl)methyl>amino>-α-(trifluoromethyl)benzenemethanol (173676-60-3)

Guidance literature:

With lithium (1R,2S)-N-pyrrolidinylnorephedrate; In tetrahydrofuran; hexane;

DOI:10.1021/ja0022728

Reference yield:

1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone (154598-53-5) → (S)-5-chloro-α-(cyclopropylethynyl)-2-<<(4-methoxyphenyl)methyl>amino>-α-(trifluoromethyl)benzenemethanol (173676-60-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / p-toluenesulfonic acid monohydrate / acetonitrile / 2 h / Heating

2: 1.) (1R,2S)-N-pyrrolidinylnorephedrine lithium alkoxide, triphenylmethane / 1.) THF, toluene, hexanes, 0-5 deg C, 30 min, 2.) THF, toluene, hexanes, -55 deg C, 60 min

With triphenylmethane; (1R,2S)-N-pyrrolidinylnorephedrine lithium alkoxide; toluene-4-sulfonic acid; In acetonitrile;

DOI:10.1021/jo981170l

upstream raw materials:

Cyclopropylacetylene

1-{5-chloro-2-[(4-methoxybenzyl)amino]phenyl}-2,2,2-trifluoroethan-1-one

cyclopropyl acetylenyllithium

4-Methoxybenzyl alcohol

Downstream raw materials:

(S)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-1-<(4'-methoxyphenyl)methyl>-3,1-benzoxazin-2-one

6-chloro-4-cyclopropylethynyl-2-(4-methoxy-phenyl)-4-trifluoromethyl-1,4-dihydro-2H-benzo[d][1,3]oxazine

6-chloro-4-cyclopropylethynyl-2-(4-methoxy-phenyl)-4-trifluoromethyl-1,4-dihydro-2H-benzo[d][1,3]oxazine

efavirenz

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