173676-60-3

Basic information

• Product Name: (S)-5-chloro-a-(Cyclopropylacetenyl)-2-[((4-methoxyphenyl)methyl)amino]-a- (trifluoromethyl) benzenemethanol (E-4)
• Synonyms: (S)-5-chloro-a-(Cyclopropylacetenyl)-2-[((4-methoxyphenyl)methyl)amino]-a- (trifluoromethyl) benzenemethanol (E-4);(S)-5-Chloro-alpha-(cyclopropylacetenyl)-2-[((4-methoxyphenyl)methyl)amino]-alpha-(trifluoromethyl)benzenemethanol;(S)-5-chloro-a-(Cyclopropylacetenyl)-2-[((4-Methoxyphenyl)Methyl)aMino]-a- (trifluoroMethyl) benzene;(S)-5-Chloro-(cyclopropylethynyl)-2-[(4-Methoxyphenyl)Methyl]aMion trifluoroMethyl benzeneMethanol;(S)-5-Chloro-α-(cyclopropylethynyl)-2-[[(4-Methoxyphenyl)Methyl]aMino]-α-(trifluoroMethyl)benzeneMethanol;BenzeneMethanol,5-chloro-a-(2-cyclopropylethynyl)-2-[[(4-Methoxyphenyl)Methyl]aMino]-a-(trifluoroMethyl)-, (aS)-
• CAS NO: 173676-60-3
• Molecular Formula: C₂₁H₁₉ClF₃NO₂
• Molecular Weight: 409.833
• Mol File: 173676-60-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 137-141ºC
• Appearance: White or light yellow crystalline powder
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: (S)-5-chloro-a-(Cyclopropylacetenyl)-2-[((4-methoxyphenyl)methyl)amino]-a- (trifluoromethyl) benzenemethanol (E-4)(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-5-chloro-a-(Cyclopropylacetenyl)-2-[((4-methoxyphenyl)methyl)amino]-a- (trifluoromethyl) benzenemethanol (E-4)(173676-60-3)
• EPA Substance Registry System: (S)-5-chloro-a-(Cyclopropylacetenyl)-2-[((4-methoxyphenyl)methyl)amino]-a- (trifluoromethyl) benzenemethanol (E-4)(173676-60-3)

Safety Data

• Hazardous Substances Data: 173676-60-3(Hazardous Substances Data)

Usage

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.

Upstream product

• 65854-91-3 N-(4-chlorophenyl)-2,2-dimethylpropionamide 
• 154598-53-5 1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone 
• 105-13-5 4-Methoxybenzyl alcohol 
• 173676-54-5 1-{5-chloro-2-[(4-methoxybenzyl)amino]phenyl}-2,2,2-trifluoroethan-1-one 
• 201218-09-9 cyclopropyl acetylenyllithium 
• 6746-94-7 Cyclopropylacetylene 

Downstream Products

• 174819-21-7 (S)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-1-<(4'-methoxyphenyl)methyl>-3,1-benzoxazin-2-one 
• 209414-26-6 6-chloro-4-cyclopropylethynyl-2-(4-methoxy-phenyl)-4-trifluoromethyl-1,4-dihydro-2H-benzo[d][1,3]oxazine 
• 209414-26-6 6-chloro-4-cyclopropylethynyl-2-(4-methoxy-phenyl)-4-trifluoromethyl-1,4-dihydro-2H-benzo[d][1,3]oxazine 
• 154598-52-4 efavirenz 

Relevant articles and documents

In situ recycling of chiral ligand and surplus nucleophile for a noncatalytic reaction: Amplification of process throughput in the asymmetric addition step of efavirenz (DMP 266)

The synthesis of efavirenz (DMP 266) involves a highly enantioselective asymmetric reaction of ketone 2a with lithium cyclopropylacetylide 3a in the presence of (1R,2S)-pyrrolidinylnorephedrine (PNE) 4b as the chiral mediator to produce 6b, a key advance

Enantioselective alkynylation of a prochiral ketone catalyzed by C2-symmetric diamino diols

C2-Symmetric diamino diols were used as chiral ligands to induce the asymmetric addition of lithium acetylides to carbonyl groups. The enantiomeric excesses (up to 99% ee) depended on the structure of the acetylene.

Use of an Ephedrine Alkoxide to Mediate Enantioselective Addition of an Acetylide to a Prochiral Ketone: Asymmetric Synthesis of the Reverse Transcriptase Inhibitor L-743,726.

The asymmetric synthesis of L-743,726 was achieved in six steps with an overall yield of 31 percent.The asymmetry was introduced using a lithiated ephedrine to mediate acetylide addition to a trifluoromethyl ketone with an enantiomeric excess of 96-98 percent.