IL27473A - Derivatives of hydroxylaminocarboxylic acids - Google Patents

Description

DERIVATIVES OP ACIDS This invention is concerned with a new class of compounds and salts and with a method for preparing More ticularly of th are represented Toy the fol lowing general formula NO wherein are class consisting of lower and X is a membe c class of droxy and a radical R wherein and are selected from a lower alkyl The process preparin the new class of compounds runs through the following 0 II COX HO COX 1 2 1 2 NO III IV The nitrone of the formula II by ting with a dilute mineral acid for a few minutes at a temperature or with hydrazine at a temperature of ving the the in is converted into the acid derivative treatment with an about equimoleoular amount of an alkali metal nitrite at acidic pH at about The starting the can be pared according to the hereinbelow described CH s CRrtC0Y HO II X have the above while Y is selected from a lower alkoxy and a group wherein and have the 3 4 3 4 above About equimolecular amounts of and a unsaturated carboxylic acid derivative of the above formula I are contacted in the presence of a basic catalyst in a lower alkanol fo a prolonged period of The if no precipitate is the sidue after complete distillation of the solvent acoording to the significance of Y in formula either a carboxylic acid ester or an In the former case the ester is at room tem perature with a solution of an alkali hydroxide in a lower liphatic As an alternative process the nitrone can be prepared reacting the with a compound of the formula R i Br C CHR COY 1 wherein R and Y have the above This second way is preferred when end compounds having a quaternary carbon at position β in respect to the carbonyl group are These owing to their acidic give salts with alkali and alkaline earth and generally with norganic and organic When X is a two different cidic functions are and both neutral and acid salts can be The compounds of the invention possess interesting tivity against various test The folloviing table gives the minimal inhibitory concentration in against some representative Strain Compound acid 1 trosohydr nic acid amino propionio acid thylamide Candida albicans 1 2 5 ATCC 10231 Candida albicans 2 2 2270 Saccharomyces 2 1 5 cerevisiae ATCC 9736 The following non limitative examples illustrate the HO NO Six grams of are heated for minutes at with 30 of per oent aqueous phuric After cooling the separated oil is tracted with diethyl and to the aqueous layer a solution of of is addedo The precipitate is filtered off and the filtrate is evaporated to dryness in vacuo The residual oil crystalli zes on yield 2 The compound is acid of the formula To a mixture of of the 15 ml of water and of acetic previously cooled to a solution of of in of water is slowl added at The aqueous after addition of is extracted diethyl ether in a continuous extraction The solvent is removed distillation and the is from isopropyl The compound is yield The starting the was prepared as lows i A mixture of 12 of of methy 5 of triethylamine and 80 of ethanol is allowed to stand for 15 days at room The mixture is evaporated to dryness in The residual oil crystalliz on standing and is recrystallized from Yield of of the formulas When allowed to stand at room temperature for one night with an equ molecular amount of sodium hydroxide in methanol the ester is hydro to the free acid with a practically quantitative Example 2 HO CH COOH 2 NO 6 5 A mixture of 18 of of hydrazine and 150 of ethanol is main tained at 4 The precipitate is Yield of To a solution of of the 100 of hydrochloric acid a solution of of in 100 of water is slowly added at The precipitate is collected and Yield 1 The produot is for days at room The mixture is evaporated to dryness in The residu oil is recrystallized from a mixture 1 of ethyl acetate and petro leum Yield 2 The compound is of the 0 From the ethyl ester the free acid is obtained by mild hy drolysis with a methanol solution sodium hydroxide Example 3 acid diethyl amide An amount of 4 of diethylamide is refluxed for 2 hours with o hydrazine and ml of then the solvent is removed The residue is dissolved in 100 of diethyl ether and the ether solution is extracted with The organic phase is carefully dried on sodium then hydrogen chloride is bubbled in causing precipitation of acid diethylamide yield To a solution of of the above hydrochloride in 130 of a solution of 45 of in of water is gradually added at The precipitate is collected and Yield 24 of acid The above was prepared as A mixture of of 2 in the usual way from atropio acid chloride and 40 of 4 of dium oxide and 300 ml of dioxane is allowed to stand for 14 days at room then the precipitate is colleoted and recrystallized from ethanol Yield of diethylamide of the mula 4 to 8 By about the same process as described ples the following compounds were aoid diethylamide of the HO NO acid of the HO COOH NO acid of the HO N CH COOH 2 NO aoid of the HO N COOH NO aoid of the HO N NO NOW particularly described and the nature of said invention and what the same to be 1 declare that insufficientOCRQuality

Claims (1)

1. A process for preparing a compound of the general formula HO COX NO wherein and are members of the class consisting of lower alkyl and X is a member of the consisting of and the radical wherein and are selected from 34 3 4 lower alkyl consisting in hydrolyzing a compou of the general formula wherein and X have the above with an agent selected from dilute mineral acids and hydrazine at a temperature o and in reacting the hydroxylaminopropionic derivative obt ned with an about equimolecular amount of an alkali metal nitrite a acidic pH at about A compound of the formula HO N COX NO wherein and are members of the consisting of hydroge lower alkyl and X is a member of the olass consisting of hydr xy1 and the radioal wherein and are seleoted lower alkyl A compound as in claim 2 of the formula HO CH CH COOH j NO A as in claim 2 of the formula HO A compound as in claim 2 of the formula insufficientOCRQuality