18108-24-2

Usage

Chemical Properties

white crystalline powder

InChI:InChI=1/C4H12NO3P/c1-3(2)4(5)9(6,7)8/h3-4H,5H2,1-2H3,(H2,6,7,8)/p-1/t4-/m1/s1

Upstream product

• 67532-85-8 isobutyrylphosphonic acid dibenzyl ester 
• 18108-23-1 diethyl 1-amino-2-methylpropylphosphonate 
• 101-02-0 triphenyl phosphite 
• 78-84-2 isobutyraldehyde 
• 148515-21-3 ethyl 2-(diethoxyphosphoryl)-3-methylbutyrate 
• 75-30-9 2-iodo-propane 
• 60064-40-6 (diethoxyphosphoryl-ethylsulfanyl-methylene)-carbamic acid ethyl ester 
• 65576-83-2 (-)-1-amino-2-methylpropylphosphonous acid 
• 35045-92-2 1-N-Benzoylamino-2-methylpropylphosphonsaeure 
• 72397-72-9 phosphono-trifluoroacetyl-valine 
• 853410-39-6 N-[1-(5,5-dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-2-methyl-propyl]-benzamide 
• 120060-85-7 [2-Methyl-1-(trityl-amino)-propyl]-phosphonic acid dimethyl ester 
• 71864-36-3 (1-amino-2-methyl-propyl)-phosphonic acid dimethyl ester; hydrochloride 
• 65577-07-3 (RS)-1-amino-2-methylpropylphosphinic acid 

Downstream Products

• 59191-42-3 1-(N-benzyloxycarbonyl)amino-2-methylpropylphosphonic acid 
• 66254-55-5 l-(1-amino-2-methylpropyl)phosphonic acid 
• 66254-56-6 (R)-(1-amino-2-methylpropyl)phosphonic acid 
• 35045-92-2 1-N-Benzoylamino-2-methylpropylphosphonsaeure 

Relevant academic research and scientific papers

Enzymes in organic chemistry. Part 9: Chemo-enzymatic synthesis of phosphonic acid analogues of L-valine, L-leucine, L-isoleucine, L-methionine and L-α-aminobutyric acid of high enantiomeric excess

Diisopropyl α-chloroacetoxyphosphonates derived from propanal, isobutanl, 3-methylmercaptopropanal, 3-methylbutanal and (S)-2-methylbutanal were resolved by enzyme-catalysed hydrolysis. Lipases preferentially hydrolysed the (S)-esters and protease Chirazyme P-2 the (R)-esters. Replacing the isopropyl groups by t-butyl groups reduced the reaction rate; replacing them by a 2,2-dimethylpropane-1,3-diyl group increased the reaction rate. (S)-α-Hydroxyphosphonates (ee 92-99%), obtained with the protease except one, were transformed into phosphonic acid analogues of L-valine, L- leucine, L-isoleucine, L-methionine and L-α-aminobutyric acid. Their enantiomeric purity was determined by HPLC on a chiral stationary phase after derivatisation at nitrogen.

1-(Acylamino)alkylphosphonic acids—alkaline deacylation

The alkaline deacylation of a representative series of 1-(acylamino)alkylphosphonic acids [(AC)-AAP: (AC) = Ac, TFA, Bz; AAP = GlyP, AlaP, ValP, PglP and PheP] in an aqueous solution of KOH (2M) was investigated. The results suggested a two-stage reaction mechanism with a quick interaction of the hydroxyl ion on the carbonyl function of the amide R-C(O)-N(H)- group in the first stage, which leads to instant formation of the intermediary acyl-hydroxyl adducts of R-C(O?)2-N(H)-, visible in the 31P NMR spectra. In the second stage, these intermediates decompose slowly by splitting of the RC(O?)2-N(H)- function with the subsequent formation of 1-aminoalkylphosphonate and carboxylate ions.

Conversion of nitriles to 1-aminophosphonic acids and preparation of phosphahomocysteines of high enantiomeric excess

A variety of nitriles was reduced to diisobutylaluminum salts of aldimines, to which diisopropyl phosphite was added. The corresponding 1-aminophosphonates were either deprotected to give racemic 1-aminophosphonic acids or reacted with Boc2O to yield N-Boc-protected 1-aminophosphonates. The enantiomers of 2-benzylthio-1-(t-butoxycarbonylamino)propylphosphonate were obtained from the racemate by chiral HPLC and converted to phosphonic acid analogs of (R)- and (S)-homocysteine, (R)- and (S)-2-aminobutyric acid and (S)-methionine, all of ee >97% as determined by chiral HPLC.

1-(N-Acylamino)alkylphosphonic acids—Deacylation in aqueous solutions

The 1-(N-acylamino)alkylphosphonic acids (AC)-AAP belong to the interesting and potentially of pharmacological importance group of 1-aminoalkylphosphonic acids derivatives. Since susceptibility of (AC)-AAP on hydrolytic deacylation can form important factor influencing their biological activity, we have undertaken deacylation investigations of these compounds in aqueous media. In this article, we present our results on deacylation of various types of 1-(N-acylamino)alkylphosphonic acids (AC)-AAP, including 1-(N-acetylamino)alkyl-phosphonic Ac-AAP, 1-(N-chloroacetylamino)alkylphosphonic acids Mca-AAP, 1-(N-trifluoroacetylamino)alkylphosphonic acids TFA-AAP, and 1-(N-benzoylamino)-alkylphosphonic Bz-AAP, derived from representative 1-aminoalkylphosphonic acids AAP (GlyP, AlaP, ValP, PglP, and PheP) in neutral and 2?M HCl solutions.

Tritylamine (triphenylmethylamine) in organic synthesis; III. The synthesis of 1-aminoalkylphosphonic acids in the reaction of N-(triphenylmethyl) alkanimines with phosphorus trichloride in acetic acid or with phosphonic (phosphorous) acid in acetic anhydride

The reaction of phosphorus trichloride in acetic acid or phosphonic (phosphorous) acid in acetic anhydride, with N-(triphenylmethyl)alkanimines gives 1-acetylaminoalkylphosphonic acids 1a-j, which after hydrolysis give 1-aminoalkylphosphonic acids 2a-j in good yields. ARKAT USA, Inc.

Cyclic chlorophosphites as scaffolds for the one-pot synthesis of α-aminophosphonates under solvent-free conditions

New α-aminophosphonates of the type (OCH2CMe 2CH2O)P(O)CH(NHCO2R)(R′) [6a-i, 7a-e, and 8a-c] have been synthesized in high yields by a three-component reaction using (OCH2CMe2CH2O)PCl (3), benzamide (or urethane or benzyl carbamate), and an aldehyde without using any catalyst under solvent-free conditions. This route can be readily adapted for bis-aminophosphonates as well as optically active binaphthoxy α-aminophosphonates; it also tolerates the phenolic -OH group as shown by the synthesis of hydroxy functionalized aminophosphonates. Partial hydrolysis of compounds 7a-d leads to products in which the phosphorinane ring is cleaved first. Compounds (OCH2CMe2CH2O)P(O)CH[NHC(O)Ph] (9-anthryl) (6f) and optically pure (R,S)-(-)-(C20H 12O2)P(O)CH(NHCO2Et)(Ph) (14a) were characterized by X-ray crystallography.

A simple synthesis of 1-aminophosphonic acids from 1-hydroxyiminophosphonates with NaBH4 in the presence of transition metal compounds

A new procedure has been developed for the synthesis of 1-aminophosphonic acids. Diethyl phosphonates are converted to hydroxyiminophosphonates when treated with hydroxylamine hydrochloride. Reduction of hydroiminophosphonates with NaBH4 in MeOH in the presence of MoO3 or NiCl2 and hydrolysis of 1-aminophosphonates gave 1-aminophosphonic acids in good yields.

Synthesis of 1-Aminoalkylphosphonic Acids via Amidoalkylation of Phosphorous Acid by N,N'-Alkylidenbisamides

N,N'-Alkylidenebisamides 1, totally unsuitable as amidoalkylating agents toward phosphorous acid, react with its "activated" form prepared "in situ" from phosphorous(III) chloride and acetic acid to give the desired 1-amidoalkylphosphonic acids 2 in high yield.

The Synthesis of 1-Aminoalkylphosphonic Acids. A Revised Mechanism of the Reaction of Phosphorus Trichloride, Amides and Aldehydes or Ketones in Acetic Acid (Oleksyszyn Reaction)

The mechanism of the amidoalkylation of trivalent phosphorus compounds in acetic acid has been reinvestigated.Evidence is presented that 1-(acylamino)alkyl acetates 5 and not N,N'-alkylidenebisamides 2 are the intermediates in this reaction.Supporting literature analogies are discussed.This paper also describes a convenient procedure for the preparation of crude (acylamino)alkyl alkanoates 5, which are excellent amidoalkylating agents.The usefulness of these reagents is demonstrated by a simple two-step "one pot" synthesis of 1-aminoalkylphosphinic acids 1.