Strychnine salts

Fructose-1,6-diphosphate (trisodium sait) [38099-82-0] M 406.1, pKj 6.14, pK 6.93 (free acid). For purification via the acid strychnine salt, see Neuberg, Lustig and Rothenberg [Arch Biochem 3 33 1943]. The calcium salt can be partially purified by soln in ice-cold M HCl (Ig per lOmL) and repptn by dropwise addition of 2M NaOH the ppte and supernatant are heated on a boiling water bath for a short time, then filtered and the ppte is washed with hot water. The magnesium salt can be pptd from cold aqueous soln by adding four volumes of EtOH. 

Preparation. The mother liquors from strychnine manufacture are concentrated and the alkaloids precipitated as neutral oxalates. The precipitate is dried and extracted with dry alcohol in which the strychnine salt is the more soluble. The less soluble salt dissolved in water is decolorised with charcoal, the alkaloid regenerated with ammonia and purified by crystallisation as the sulphate. According to Saunders, pure brucine may be obtained by slow crystallisation from a solution of the pure hydrochloride in alcoholic ammonia. A method of separation depending on the greater solubility in water of strychnine hydriodide was employed by Shenstone, whilst others have made use of the sparing solubility of strychnine chromate for the removal of small quantities of this alkaloid from brucine. For a large scale process see Schwyzer. ... 

Faolini and Divizia have succeeded in partially resolving inactive linalol into its optically active isomers hut only to the extent of optical rotations of + 1° 70 and — 1° 60 respectively. Linalol was converted into its acid phthalate, and an alcoholic solution of this compound was treated with the equivalent quantity of strychnine. By fractional crystallisation the laevo-rotatory salt, yielding dextro-rotatory linalol, separates first, leaving the more soluble dextro-rotatory strychnine salt, which yielded laevo-rotatory linalol in the mother liquor. 

Paolini has separated from the reduction products of thujone the acid phthalate of / -thujyl alcohol, HOOC. C H. COO. Cj(,Hjj, melting at 120°, and having a specific rotation -t- 91 27°. This body yields a silver salt which melts at 85° to 86°, and a strychnine salt melting at 177° to 178°. On saponifying the phthalate y8-thujyl alcohol results, which has the following characters —... 

No isomer appeared to be present in savin oil, since no separation could be effected by conversion of the hydrogen phthalate into its strychnine salt, and fractional crystallisation thereof. The strychnine salt, CggH OgNj, melts at 200° to 201°. 

Rh(C204)3 was resolved by Werner as the strychnine salt but other ions, such as Coen3+ and Niphen3+, have been used more regularly for this [84]. 

Chromium, tris(hexafluoroacetylacetonato) optical isomerism, 1, 28 Chromium, tris(oxalato)-raceinization solid state, 1,466 strychnine salt... 

Rh(C204)3 was resolved by Werner as the strychnine salt but other ions, such as Coen3+ and Niphen3+, have been used more regularly for this [84], The dinuclear rhodium(II) acetate is described in section 2.8.2 the dinuclear structure is retained on one-electron oxidation, but when ozone is used as the oxidant, a compound with a trinuclear Rh30 core is formed, analogous to those formed by Fe, Cr, Mn and Ru. (It can also be made directly from RhCl3.)... 

KaFe(CN)6 or K2Cr04—Yellow crystalline ppt. in neutral and fairly cone, strychnine salt solution. 

Busch and Bailar1 obtained optically active solutions of one of the enantiomers of the ethylenediaminetetraacetato-cobaltate(III) ion by selective adsorption on optically active quartz and by fractional crystallization of the strychnine salt. More recently Dwyer, Gyarfas, and Mellor2 reported the complete resolution using d and Z-tris(ethylenediamine) cobalt(III) chloride. Precipitation of the diastereoisomers was effected by addition of ethanol to the aqueous solution. The volume of ethanol used was critical and often merely the potassium salt separated. 

This is best separated by means of the strychnine salts. 13.3 g. of the crystals and 23 g of strychnine are dissolved in 300 cc. of hot water and allowed to stand over night in the ice box. The strychnine salt of d-benzoylalaiune separates as thick platelets, but must be recrystallized four times from the same volume of water before the optical rotation reaches a constant value and all traces of the Z-compound are eliminated. The yield should then be about 20 g. 

A solution of the pure strychnine salt in 600 cc. of water is made alkaline with 40 cc. of normal sodium hydroxide solution and chilled The strychnine is filtered off and the filtrate acidified with 40 cc. of normal acid and concentrated to small bulk in vacuo. 5 g. of pure d-benzoylalanine separate on cooling. The... 

Strychnine salt Quinine salt Brucine salt... 

Studies were carried out both with chiral ethanol and chiral neopentanol. " Figure 12 shows the anionic phthalate half-ester of (-F)-neopentyl-l- f alcohol crystallized as its strychnine salt. In this study the absolute configuration of the -0-CHD-C(CH3)3 group was determined to be (S) (Figure 12). 

Levo Lactic Acid.— Levo lactic acid was first obtained by the fermentation of cane sugar by specific bacteria. It is levo rotatory but, like the dextro acid, the rotation of its salts and its anhydride is reversed, being dextro rotatory. The levo lactic acid and also the dextro acid may be obtained by splitting the inactive acid into its optical components by means of its strychnine salt. 

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