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Large-Scale Synthesis of Diammonium Acetyl Phosphatel

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Large-Scale Synthesis of Diammonium Acetyl Phosphatel [Reprinted from the Journal of Orsanic Chemistrv. 10, 2516(1975i.1 Copyright 1975by the American Chemical Society and reprinted b!' permissionrf the copyright owner. Large-Scale Synthesis of Diammonium Acetyl Phosphatel George M. Whitesides,* Merrell Siegel, and Patricia Garrett Department of ChemistrTt,Massachusetts Institute of Technology, Cambridge, Massachusetts 02139 ReceiuedApriL 11,1975 A detailed procedure for the large-scale synthesis of diammonium acetyl phosphate (1) is presented. Ketene is used to acylate 1007ophosphoric acid in ethyl acetate at -10o, and the resulting mixture of mono- and polyacetyl phosphoric acids converted to I by treatment with anhydrous ammonia in ethyl acetate-methanol at -10o. The product is obtained as an easily filtered, crystalline solid in ca. 90% yield and ca. 90% purity. One limitation to the use of enzymatic catalysis in large- ADP is produced from ATP and AMP by phosphoryl scale organic synthesis has been the expense of many of the transfer catalyzed by adenylate kinase. ADP is converted common cofactors. As part of an effort to devise techniques to ATP by reaction with acetyl phosphate (AcP) catalyzed that would make enzymatically catalyzed reactions requir- by acetate kinase. Acetyl phosphate, the ultimate phospho- ing adenosine triphosphate (ATP) useful in practical syn- rylating agent in this sequence, had been synthesized pre- thesis, we have developed the reaction sequenceoutlined in viously from phosphoric acid by acylation with acetyl chlo- eq 1 and 2 as a method for regenerating ATP from AMP ride,3 ketene,a isopropenyl acetate,5 and acetic anhy- and/or ADP.2 dride,6'? and isolated as the lithium or silver salts.8 All of these procedures contain difficult work-up and isolation se- + Arp AMp #- 2ADp (1) quences. None are suitable for the preparation of acetyl phosphate in large quantity. Here we report a synthesis of 2ADP + 2AcP 2ATP + 2Ac (2) :-kinase diammonium acetyl phosphate from phosphoric acid, ke- Synthesis of Diammonium Acetyl Phosphate I Ors Chem., Vol. 40, No. 17, 1975 2517 tene, and ammonia, which yields product in easily isolated this studv are summarized in Figure 1 for acylations of form. This synthesis provides the most practical method both 85 and 100o/ophosphoric acid. These data establish available for synthesizing large quantities of acetyl phos- that the maximum conversion (90-95ozn)of 100o/"phosphor- phate. ic acid to 1 occurs for molar ratios of ketene to phosphoric Results acid of approximately 1.7. The decreasein yield observed The reaction of ketene with phosphoric acid in an inert solvent yields mono-, di-, and (presumably) triacetylphos- phoric acids.The relative amount of monoacetylphosphoric acid produced depends on the ratio of reactants used and on the extent of hydration of the phosphoric acid: water that is present is converted to acetic acid and acetic anhy- dride. Dilution of the reaction mixture obtained from ke- tene and phosphoric acid with methanol, and treatment of the resulting solution with anhydrous ammonia at -10o, yields diammonium acetyl phosphate (l) as an easily fil- tered, crystalline solid. CH.:C--C + H,pO: l+ H.Ol -i ) oo il CH COPO.H. + {CH CO).PO H + o oo llri' (cHrco) ,Po [+ cH ]co"H + cH coccH j oo o o cHTc=o/ H3Pc.4 lllillrl CH.COP(O-NHr.).+ CH,CNH. [* CH CO-NH,.l (3) Figure l. \'ields of diammoniumacetyl phosphate obtained fol- lowingreact.ion ofketene with l00o/ophosphoric acid (o) and 859. 1 phosphoricacid (t). Reactionswere carried out in ethyl acetate Isolation of acetyl phosphate as its diammonium salt has solutionat -1{)o,and the reactionmixtures were allowed to equili- a number of advantages over other isolation procedures. brate for 2 hr at -l0o beforediluting with methanoland adding 'fhe (CHz:C:O/H:IPO+) First, I is sparingly soluble in methanolic solutions, and ammonia. quantity is the number of added.divided bv the total numberof moleso{' precipitates as a crystalline, easily filterable solid. Ammo- molesol'ketene phosphoricacid originallvpresent. In 85% phosphoricacid, 1 mol soluble in methanol and nium acetate and acetamide are of wateris presentfor eachmole o|phosphonc acid. Yields are can be separated on the basis of solubilities. Previous pro- basedon phosphoricacid. The numbers associatedwith each cedures have involved neutralization of the acetylphospho- pointrepresent the ptrritvof the I isolatedat that ptiint;themajor ric acid in aqueous solutions, and have required either the partof the impuritt isammonium phosphate in mostinstances. use of silver(l) salts to effect precipitation or the filtration of the phosphate "slimes" generated by neutralization with for ratios greater tlu . 2 reflects the fact that addition of lithium acetate, carbonate, or hydroxides, followed by pre- ammonia t.othese reactions yields thick, difficultly filtered cipitation with ethanol. In addition, removal of water from suspensions.The use of 85olnphosphoric acid gave lower the dilithium acetyl phosphate required a time-consuming yields, apparently for the same reason. The effects of sol- and not always successfullyophilization or related proce- vent. phosphoric acid water content, and temperature on dure. Second, ammonia is expected to attack the acetyl yields of I were examined briefly: 100o/ophosphoric acid, moiety of diacetyl phosphate more rapidly than that of mo- prepared bv dehydration of 85o/"phosphoric acid,rl gave noacetyl phosphate.eThis appears to underlie the unexpec- higher vields than dioxane diphosphate or 85o/ophosphoric tedly high yields ()90o/o)of I obtained by this procedure. acid; ethyl acetate was superior as a solvent to DMF, DME, Although we have not studied the reactions that occur dur- di-n-butyl ether, and n-butyl acetate;raising the tempera- ing introduction of ammonia into the initial reaction mix- ture above -10o during addition of ketene and equilibra- tures in any detail, it seems that the excessof ammonia tion resulted in lower yields. present at the conclusion of this stage must convert di- and The detailed course of the acylation of phosphoric acid triacetyl phosphates to l. Third, 1 is very soluble in water, with ketene has not been established.l2In particular, it is and ammonium ion is innocuous to most (although not all) not clear how rapidly intermolecular acyl or acetyl group enzymes.l0Thus I can be used directly in the regeneration transfer occurs. A qualitative observation made during this of ATP. Ammonia is inexpensive compared with lithium work does, however, suggestthat intermolecular equilibra- and silver salts. Finally I has adequate storageand solution tion between diacetyl phosphoric acid and phosphoric acid stability (vide infra). occurs under the reaction conditions. A sample of 100o/o The number of products that can be formed by reaction phosphoric acid was allowed to absorb 2 molar equiv of ke- of ketene with phosphoric acid containing some water is tene. The resulting sarnple was treated with 1 additional large. This complexity, combined with uncertainties con- equiv of phosphoric acid, allowed to equilibrate at -10o for cerning the details of this reaction and of the subsequent 2 hr, and then worked up by the usual procedure,yielding I reaction of the product mixture with ammonia, make it dif- in72v" yield based on the fofol phosphoric acid involved in ficult to define a priori the number of equivalents of ketene the mixture. Since the initial reaction mixture would have required to maximize conversion of phosphoric acid to di- yielded ca. 45o/nof | (90o/ol2)on this basis had equilibration ammonium acetyl phosphate. In this work, the ratio of not occurred, the higher yield-which is also that obtained added ketene to phosphoric acid originally present has sim- by direct reaction of 2 equiv of ketene with 2 equiv of phos- ply been varied, and the yield of I determined. Results of phoric acid-suggests intermolecular equilibration. 2518 J Org Chem., Vol. 40, No. 17, 1975 Whitesides, Siegel, and Garrett o o NMR assays.A Radiometer Model PHM 62 pH meter was used to determine pH values. Microanalysis were obtained by Midwest (CHTCO)"PO'H+ HrPOr r- zCHTCOPOTH" (4) Microlab, Ltd., Indianapolis, Ind. Diammonium Acetyl Phosphate (l). A 2-1.three-necked flask Ammonium ion, although normally innocuous as a com- was fitted with a thermometer, a gas inlet tube, and an overhead ponent of an enzymatic reaction mixture, does occasionally stirrer. The stirrer shaft entered the flask through a fitting reduce enzymatic activity,l0 and might interfere with other equipped with a side arm which served as a gas outlet. Ethyl ace- aspects of a synthetic sequence catalyzed by enzymes. It is tate (750 ml) and 100% phosphoric acid (100 g, 1.02 mol) were possible to convert I to disodium acetyl phosphate by transferred into the flask. and the resulting solution was cooled to -10o using an ethylene glycol-acetone-Dry Ice bath. Ketene was treatment with an ion exchange resin in water, although bubbled through the stirred solution for 10 hr (1.98 mol), after the yield is only moderate by the procedure we employed. which 750 ml of methanol, precooled to -10o, was added. Anhy- It is also possible to use other amines (e.g.,aniline) to neu- drous ammonia, directly from the tank, was passed through alumi- tralize the initial reaction mixture. The salts resulting from num coils immersed in the cooling bath, then over the surface of these reactions are less crystalline and more soluble in the rapidly stirred solution, and finally out through a bubbler methanol, and this type of work-up offers no obvious ad- linked to the flask through the gas outlet on the stirrer. This addi- tion was continued for 1.5 hr at a rate such that bubbles passed vantages. through the outlet bubbler at a rate of approximately one per sec- Compound I does contain a potential nucleophile (am- ond. During this time, the internal temperature of the solution monia) in the presenceof a reactive carbonyl group, and it graduall-"-rose to -7o and then fell to -10o, signalling the end of was important to examine its stability.
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