83648-76-4

Basic information

• Product Name: (2S)-2-<4-(trans-(1R,2S)-2-hydroxycyclopentylmethyl)phenyl>propionic acid
• Synonyms: (2S)-2-<4-(trans-(1R,2S)-2-hydroxycyclopentylmethyl)phenyl>propionic acid
• CAS NO: 83648-76-4
• Molecular Weight: 248.322
• Mol File: 83648-76-4.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (2S)-2-<4-(trans-(1R,2S)-2-hydroxycyclopentylmethyl)phenyl>propionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-<4-(trans-(1R,2S)-2-hydroxycyclopentylmethyl)phenyl>propionic acid(83648-76-4)
• EPA Substance Registry System: (2S)-2-<4-(trans-(1R,2S)-2-hydroxycyclopentylmethyl)phenyl>propionic acid(83648-76-4)

Safety Data

• Hazardous Substances Data: 83648-76-4(Hazardous Substances Data)

Upstream product

• 89675-47-8 methyl 2-<4-(trans-2-acetoxycyclopentylmethyl)phenyl>propionate 
• 89631-53-8 methyl 2-<4-(cis-2-acetoxycyclopentylmethyl)phenyl>propionate 
• 83599-42-2 (2S)-2-<4-((1R)-2-oxocyclopentylmethyl)phenyl>propionic acid 
• 72748-99-3 (R)-1-Amino-2-(methoxymethyl)pyrrolidine 
• 589-29-7 p-xylylene glycol 
• 1333080-48-0 4-((4-methoxybenzyloxy)methyl)benzaldehyde 
• 1333080-45-7 (R)-2-[4-((S)-2-hydroxy-1-methylethyl)benzyl]cyclopentanone 
• 1333080-43-5 C₃₁H₃₈O₂Si 
• 1333080-42-4 [(S)-2-(4-bromomethylphenyl)propoxy]-tert-butyldiphenylsilane 
• 1333080-41-3 {4-[(S)-2-(tert-butyldiphenylsilanyloxy)-1-methylethyl]phenyl}methanol 
• 1333080-40-2 tert-butyl{(S)-2-[4-(4-methoxybenzyloxymethyl)phenyl]propoxy}diphenylsilane 
• 1333080-39-9 (S)-2-(4-(4-methoxybenzyloxy)phenyl)propan-1-ol 
• 1333080-31-1 (4-((4-methoxybenzyloxy)methyl)phenyl)methanol 
• 1333080-37-7 C₂₀H₂₄O₄ 

Downstream Products

• 88378-29-4 {2-[4-((1R,2S)-2-Acetoxy-cyclopentylmethyl)-phenyl]-propionylamino}-acetic acid ethyl ester 
• 88378-26-1 2-{2-[4-((1S,2R)-2-Hydroxy-cyclopentylmethyl)-phenyl]-propionylamino}-ethanesulfonic acid 
• 88378-27-2 {2-[4-((1S,2R)-2-Hydroxy-cyclopentylmethyl)-phenyl]-propionylamino}-acetic acid 
• 290331-99-6 Acetic acid (1S,2R)-2-{4-[(S)-1-((S)-1-phenyl-ethylcarbamoyl)-ethyl]-benzyl}-cyclopentyl ester 
• 88378-28-3 2-[4-((1R,2S)-2-Acetoxy-cyclopentylmethyl)-phenyl]-propionic acid 
• 89631-57-2 methyl (+/-)-2-<4-(cis-2-hydroxycyclopentylmethyl)phenyl>propionate 
• 89631-57-2 methyl (+/-)-2-<4-(trans-2-hydroxycyclopentylmethyl)phenyl>propionate 

Relevant articles and documents

Asymmetric synthesis of the active form of loxoprofen and its analogue

The asymmetric synthesis of the active form of the antiinflammatory drug loxoprofen has been reported in this article. Enzymatic kinetic resolution/racemization of a substituted homo-benzylic primary alcohol with lipase-PS, asymmetric alkylation of cyclic ketones using either Enders' or Meyers' strategy followed by a stereoselective biocatalytic reduction of carbonyl group are the key reactions employed successfully to achieve the target molecule and one of its analogue.

Synthesis of the active form of loxoprofen by using allylic substitutions in two steps

High regioselectivity for allylic substitution of the cyclopentenyl picolinate 5 with benzylcopper reagent was attained with ZnBr2, and the finding was applied to the p-BrC6H4CH2 reagent. The cyclopentene moiety in the product was reduced to the cyclopentane, and the p-BrC6H4 was converted to the "Cu"C6H4 for the second allylic substitution with picolinate 8 to furnish the title compound after oxidative cleavage of the resulting olefin moiety.

An efficient synthesis of (2S)-2-[4-((1R, 2S)-2- hydroxycyclopentylmethyl)phenyl]propionic acid

An efficient synthesis of (2S)-2-[4-((1R,2S)-2- hydroxycyclopentylmethyl)phenyl]propionic acid via lipase-catalyzed kinetic resolution of (-)-N-[(1S)-1-phenylethyl]-(±)-2-[4-(trans-2- hydroxycyclopentylmethyl)phenyl] propionamide is successfully accomplished.