D-alpha-Cyclohexylglycine
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D-alpha-Cyclohexylglycine
structure -
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CAS No:
14328-52-0
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Formula:
C8H15NO2
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Chemical Name:
D-alpha-Cyclohexylglycine
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Synonyms:
(R)-2-Cyclohexylglycine;D-CHG-OH;D-αD-Chg-OH·TFA;D-Cyclohexylglycine,99%e.e.;(R)-CYCLOHEXYLGLYCINE;(R)-AMINO-CYCLOHEXYL-ACETIC ACID;(R)-(+)-ALPHA-AMINOCYCLOHEXYLACETIC ACID
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CAS No:
Description
white powderD-alpha-Cyclohexylglycine is a kind of non-proteinogenic amino acid. It is widely presented in various natural products and pharmaceutical intermediates. It can be incorporated into the peptide inhibitors renders resistance from peptidases and proteinases and thereby imparts pharmacological stability to molecules. Some derivatives of Cyclohexylglycine has been recently been developed into inhibitors of the dipeptidyl peptidase-IV enzyme (“DP-IV inhibitors”) and which are useful in t
Characteristics
63.3
-1
Solid
1.120±0.06 g/cm3(Predicted)
256 °C
292.8±23.0 °C(Predicted)
130.9±22.6 °C
1.510
Soluble
2-8°C
-34.5 º (c=0.4 5N HCl)
D-alpha-Cyclohexylglycine Use and Manufacturing
Experimental examples: Production of D-cyclohexylglycine 100 g (661.5 mmol) D-phenylglycine are dissolved or suspended in 890 ml deionised water, 290 ml isopropanol and 66.7 ml (802 mmol) 37 percent hydrochloric acid. After addition of 10 g of the Pt/Rh catalyst, 4 percent Pt + 1 percent Rh on activated carbon (water content approx. 50 percent, corresponding to approx. 5 wt. percent catalyst relative to D- phenylglycine used), the reaction mixture is introduced into a 2 1 hydrogenation autoclave. After being rendered inert with nitrogen three times, it is rinsed with hydrogen twice, then a hydrogen overpressure of 8-10 bar is established and the reaction solution heated to 50- 60°C. After approximately 6 to 8 hours, hydrogen uptake is completed (theoretical amount of H2 44.4 1). The hydrogenator is depressurised and once again rendered inert with nitrogen three times. The still hot reaction solution is extracted with a nutsch filter and the catalyst is washed with 200 ml deionised water. The filtrate is first adjusted at 40-60°C to a pH of 2-2.5 with 50percent sodium hydroxide solution, during which process the first crystals form. It is then stirred for a further 15-30 minutes at this pH and then adjusted to a pH of 5-6 with 50percent sodium hydroxide solution. The reaction mixture is cooled in an ice bath to a temperature of 0-10°C, the product is extracted with a nutsch filter, washed with 300 ml deionised water and dried in a drying oven in vacuo at 50-70°C. The CATALYST. ;, , CAN be reused several times with no loss of activity. Yield: 100-OLD2 g (95.8-97. 7 percent) H-NMR (500 MHz, D20/NAOD) : 8 (PPM) = 1-1. 26 and 1.53-1. 75 (each m, together 11H, cyclohexyl H), 3.02 (d, 1 H, A-H) In all the cases analysed, the enantiopurity of the D- cyclohexylglycine produced in this way (determined by GC with chiral separation phases) was identical to the enantiopurity of the D-phenylglycine used.
Computed Properties
Molecular Weight:157.21
XLogP3:-1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:157.110278721
Monoisotopic Mass:157.110278721
Topological Polar Surface Area:63.3
Heavy Atom Count:11
Complexity:141
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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