Cyclohexylacetic acid

The retro-synthetic analysis ouflined in Scheme 6.1 shows that in addition to the Pictet-Spengler route previously used by discovery, several others are also possible. The Bischler-Napieralski condensation of 5-methyltryptamine and 2-cyclohexylacetic acid chloride as well as the Friedel-Crafts reaction of the N-protected 5-methyltryptamine allows preparation of the prochiral imine derivative 7. The 2-cyclohexylmethyl side chain may also be introduced via alkylating an unsubstituted THpC by 2-cyclohexylmethyl chloride. As shown in Scheme 6.1, all of these routes involve 5-methyltryptamine as a common building block. 

Hydrogenation of a benzene ring. Hydrogenation of (R)-a-phenylglycine with Pd/C in aqueous alkaline solution results in formation of phenylacetic acid, but use of Pd(OH)a/C leads to (R)-a-cyclohexylglycine (40-60% yield 84% ee) and cyclohexylacetic acid (35-55%, yield). ... 

Figure 9.28. The diffusion titration curves for the binding of the host /3-CD 9.4 with the guests (a) cyclohexylacetic acid 9.2 (K = 1800and (b) cholic acid 9.3 ( fa = 5900M ) (adapted with permission from [39], Copyright 2001, American Chemical Society).

Synonyms Allyl cyclohexylacetate Cyclohexylacetic acid allyl ester 2-Propenyl cyclohexaneacetate... 

Cyclohexylacetic acid ethyl ester. See Ethyl cyclohexylacetate Cyclohexyl acrylate CAS 3066-71-5... 

Synonyms Cyclohexaneacetic acid, ethyl ester Cyclohexane ethyl acetate Cyclohexylacetic acid ethyl ester Ethyl cyclohexaneacetate... 

TABLE 113 Experimental and Predicted Metabolic Liabilities in Human Liver Microsomes of a Series of DGATl Inhibitors with a Cyclohexylacetic Acid (R) as Common Pharmacophore... 

FIGURE 11.5 (a) A series of DGATl inhibitors with a benzylamidothiadiazole scaffold sharing a cyclohexylacetic acid as common pharmacophore, (b) Analysis of compound 4 with MetaSite3 [99]. The proposed main metabolite is the aliphatic hydroxylation product at the SOM. The scores plot ranks the thiadiazole alpha position on top of aU substrate sites (blue bar). Most probable SOM are color coded in a structure diagram (blue circle). For color details, please see color plate section. 

Macronecine, K22.12 Platynecine, K22.7 Dihydroxyheliotridane, K22.14 2-Amino-2-cyclohexylacetic acid, A23.15 Homostachydrine, A"6.4 C8H15NO2S2... 

Acetoxy-2-cyclohexylacetic acid. A 19.10 2,2,3-Trimethyl-4-oxocyclohexanecarboxylic acids, A 21.15... 

Fig. 10.8 Computer docking experiment of host 1 with guest, cyclohexylacetic acid.

Cyclohexylacetic acid (CgHi 02), HL 4-Methylphenylacetic acid 9%0°2 HL 4-Ethylphenylacetic acid (C10H12O2). HL... 

The HCl salt of A-butyl-iV-(cyclohexylethyl)amine (2 HC1) was synfiiesized firom commercially available cyclohexylacetic acid (11). Acid chloride formation using thionyl chloride in toluene with catalytic DMF was followed by amine acylation under Schotten-Baumann conditions to give the amide (8). After workup, the resulting toluene solution was azeotropically dried and the amide was reduced with BH3 SMe2. The crude reaction mixture was quenched with HCl in MeOH and the resulting salt was crystallized from toluene/MTBE. The salt was isolated in 80% yield for the 3 steps. 

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