* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With lithium aluminium tetrahydride In tetrahydrofuran at 20 - 80℃; for 4 h;
Step 1: To a stirred mixture of LiAlH4 (724 mg, 19.08 mmol) in anhydrous THF (20 mL) at rt was addedportionwise 2-cyclohexyl-D-glycine (1 g, 6.36 mmol). The mixture was heated at 80 °C for 4 h. The mixture was cooled to 0 °C and then water (1 mL), 1M aq NaOH (1 mL), and water (3 mL) were added sequentially. The mixture was filteredand the filtrate was partitioned between a mixture of DCM, 1M aq NaOH, and saturated aq sodium potassium tartrate.The organic layer was separated and further washed with 1M aq NaOH. The organic was separated, dried over MgSO4filtered, and concentrated under reduced pressure to afford (R)-2-amino-2-cyclohexylethanol (400 mg) which was notpurified further. LCMS (ESI) m/z 144 (M+H)+.
Reference：
[1] Chemische Berichte, 1986, vol. 119, # 7, p. 2191 - 2207
[2] Journal of Organic Chemistry, 1983, vol. 48, # 13, p. 2195 - 2202
[3] Patent: EP2766359, 2016, B1, . Location in patent: Paragraph 0536
2
[ 875-74-1 ]
[ 14328-52-0 ]
Yield
Reaction Conditions
Operation in experiment
95.8%
With hydrogenchloride; hydrogen In water; isopropyl alcohol at 50 - 60℃; for 6 - 8 h;
Experimental examples: Example 1: 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.
Reference：
[1] Patent: WO2005/14526, 2005, A1, . Location in patent: Page/Page column 12
[2] Chemische Berichte, 1986, vol. 119, # 7, p. 2191 - 2207
[3] Journal of Organic Chemistry, 1983, vol. 48, # 13, p. 2195 - 2202
[4] Justus Liebigs Annalen der Chemie, 1936, vol. 523, p. 199,203
[5] Il Farmaco; edizione scientifica, 1971, vol. 26, # 5, p. 474 - 486
3
[ 63546-36-1 ]
[ 14328-52-0 ]
Reference：
[1] Journal of the American Chemical Society, 1982, vol. 104, # 1, p. 363 - 365
4
[ 54750-25-3 ]
[ 14328-52-0 ]
[ 76249-99-5 ]
Reference：
[1] Journal of the American Chemical Society, 1982, vol. 104, # 1, p. 363 - 365
5
[ 5664-29-9 ]
[ 14328-52-0 ]
Reference：
[1] Journal of the Chemical Society, 1957, p. 2073,2077
[2] Collection of Czechoslovak Chemical Communications, 1966, vol. 31, p. 4563 - 4580
6
[ 2935-35-5 ]
[ 14328-52-0 ]
Reference：
[1] Journal of Medicinal Chemistry, 1977, vol. 20, # 2, p. 279 - 290
7
[ 5963-46-2 ]
[ 14328-52-0 ]
Reference：
[1] Journal of the Chemical Society, 1957, p. 2073,2077
8
[ 14429-43-7 ]
[ 14328-52-0 ]
Reference：
[1] Collection of Czechoslovak Chemical Communications, 1966, vol. 31, p. 4563 - 4580
9
[ 59759-91-0 ]
[ 14328-52-0 ]
Reference：
[1] Journal of the Chemical Society, 1957, p. 2073,2077
10
[ 24424-99-5 ]
[ 14328-52-0 ]
[ 70491-05-3 ]
Reference：
[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4815 - 4830
[2] Patent: WO2004/22534, 2004, A1, . Location in patent: Page 53; 54
With hydrogenchloride; hydrogen; In water; isopropyl alcohol; at 50 - 60℃; for 6 - 8h;
Experimental examples: Example 1: 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 % hydrochloric acid. After addition of 10 g of the Pt/Rh catalyst, 4 % Pt + 1 % Rh on activated carbon (water content approx. 50 %, corresponding to approx. 5 wt. % 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- 60C. 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 40-60C to a pH of 2-2.5 with 50% 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 50% sodium hydroxide solution. The reaction mixture is cooled in an ice bath to a temperature of 0-10C, the product is extracted with a nutsch filter, washed with 300 ml deionised water and dried in a drying oven in vacuo at 50-70C. The CATALYST. ;,, CAN be reused several times with no loss of activity. Yield: 100-OLD2 g (95.8-97. 7 %) 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.
With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 - 80℃; for 4h;
Step 1: To a stirred mixture of LiAlH4 (724 mg, 19.08 mmol) in anhydrous THF (20 mL) at rt was addedportionwise <strong>[14328-52-0]2-cyclohexyl-D-glycine</strong> (1 g, 6.36 mmol). The mixture was heated at 80 C for 4 h. The mixture was cooled to 0 C and then water (1 mL), 1M aq NaOH (1 mL), and water (3 mL) were added sequentially. The mixture was filteredand the filtrate was partitioned between a mixture of DCM, 1M aq NaOH, and saturated aq sodium potassium tartrate.The organic layer was separated and further washed with 1M aq NaOH. The organic was separated, dried over MgSO4filtered, and concentrated under reduced pressure to afford (R)-2-amino-2-cyclohexylethanol (400 mg) which was notpurified further. LCMS (ESI) m/z 144 (M+H)+.
(R)-[(tert-butoxycarbonyl)amino](cyclohexyl) acetic acid (1.20g, 73%) was isolated as a white foam from (R)-1-amino-1-cyclohexyl carboxylic acid (1. [0G,] 6. [36MOL),] tetramethylammonium hydroxide (2.31g, 12. [7MMOL)] and (BOC) 20 (2.92mL, 12. [7MMOL).]
With methanesulfonic acid; benzyl alcohol; In toluene;
(a) Benzyl (2R)-2-amino-2-cyclohexylethanoate methanesulfonate To a suspension of (2R)-2-amino-2-cyclohexylethanoic acid (200 g, 1.27 mol) and benzyl alcohol (276 g, 2.54 mol) in toluene (1600 mL) was added methanesulphonic acid at a rate which did not allow the temperature to reach 100 C. The reaction was stirred for an additional six hours at between 110 and 115 C. The water that was produced was distilled off using a Dean-Stark trap. An additional portion of benzyl alcohol (276 g, 2.54 mol) was added and the mixture was refluxed for a further twelve hours with water distillation. The reaction mixture was then cooled and methyl tert-butyl ether was added to initiate crystallisation. The product was filtered and dried to yield 404 g (92%) of the sub-title compound.
With hydrogen bromide; sodium nitrite; In water; at 0℃; for 2.5h;
The <strong>[14328-52-0](R)-2-amino-2-cyclohexylacetic acid</strong> (H-Cyclohexyl-D-Gly-OH, 1 g, 6.36 mmol), which is commercially available from Bachem California Inc., Torrance, Calif. 90505, was dissolved in a mixture of HBr 48% ( 5.8 niL, 50.9 mmol) and H2O (20 mL). At 0 C., a solution of NaNO2 (1.4 g, 20.4 mmol) in H2O (10 mL) was added over a period of 30 min. The reaction was stirred for two hours. The reaction mixture was degassed in vacuo and extracted with EtOAc (2×2mL). The extracts were washed with water (15 mL), dried (Na2SO4), filtered and evaporated to give 1.3 g (92% yield) of the (R)-2-bromo-2-cyclohexylacetic acid as a white solid.
(R)-2-cyclohexyl-2-(3-methylbenzamido)acetic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
50%
With sodium hydroxide; In water; at 0℃; for 0.166667h;
(R)-2-Cyclohexyl-2-(3-methylbenzamido)acetic acidTo a solution of <strong>[14328-52-0](R)-2-amino-2-cyclohexylacetic acid</strong> (1DO mg, 0.636mmol) in a 20% aqueous sodiumhydroxide solution (2 ml) was addeddropwise 3-methylbenzoyl chloride (110 mg, 0.709 mmol) at 0C. The mixture was stirred for 10 minutes before the reaction was quenched with ice-water (10 ml). The pHof the mixturewas adjusted to 1 by addition ofa 37% aqueous hydrochloric acid solution. The mixture 15 was extracted with ethyl acetate (3 x 100 ml). The combined organic layers were dried over anhydroussodium sulfate and the solvent was removed under reduced pressure.The residue waspurified by silica gel column chromatography eluting withdichloromethane : methanol = 20:1 to afford (R)-2-cyclohexyl-2- (3-methylbenzamido)acetic acid as a colorless oil (87 mg, 50%).LCMS (ESI): m/z= 276.2 [M+H(
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