10314-06-4

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-Phthalimido)butanoyl chloride is used as a reagent for the preparation of pharmaceutical intermediates. Its reactivity allows for the synthesis of various compounds that can be further utilized in the development of drugs and medications.
Used in Specialty Chemicals Industry:
In the specialty chemicals sector, 1-(2-Phthalimido)butanoyl chloride serves as a key component in the production of specific chemicals. Its unique properties enable the creation of tailored chemical products for niche applications, such as in coatings, adhesives, or other industrial materials.

InChI:InChI=1/C12H10ClNO3/c13-10(15)6-3-7-14-11(16)8-4-1-2-5-9(8)12(14)17/h1-2,4-5H,3,6-7H2

Upstream product

• 85-44-9 phthalic anhydride 
• 56-12-2 4-amino-n-butyric acid 
• 22509-74-6 N-ethoxycarbonylphthalimide 
• 1074-82-4 potassium phtalimide 
• 3130-75-4 4-phthalimidobutyric acid 

Downstream Products

• 3459-33-4 4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)butyramide 
• 41306-64-3 2-(5-bromo-4-oxo-pentyl)-isoindole-1,3-dione 
• 173375-29-6 N-<4-<(1,3-Dihydro-5-methyl-2-oxo-3H-imidazol-4-yl)carbonyl>phenyl>-4-phthalimidobutanamide 

Relevant academic research and scientific papers

Synthesis of pyrazoles based on functionalized allenoates

Regiospecific synthesis of pyrazole-3-carboxylate derivatives by 1,3-dipolar cycloaddition of diazomethane with allenoates in presence of triethylamine is demonstrated. Reaction of allenoates with stearic acid moiety containing diazoketone is explored under ultrasonic conditions. Novel derivatives of pyrazole were achieved in excellent yields.

Primary, Secondary, and Tertiary γ-C(sp3)-H Vinylation of Amides via Organic Photoredox-Catalyzed Hydrogen Atom Transfer

An efficient strategy for primary, secondary and tertiary aliphatic γ-C(sp3)-H vinylation of amides with alkenylboronic acids is reported. These reactions are catalyzed by visible-light organic photoredox agents. Regioselective γ-C(sp3)-H vinylation of amides is controlled by a 1,5-hydrogen atom transfer of an amidyl radical generated in situ.

Synthesis and anticonvulsant activity of N,N-phthaloyl derivatives of central nervous system inhibitory amino acids

In order to study the influence of the length of the amino acid chain of N,N-phthaloyl-amino acid amides as analogues of the former anticonvulsant taltrimide on the seizure-antagonizing activity glycine, β-alanine and γ-aminobutyric acid (GABA) derivatives were synthesized. The corresponding taurine derivatives were also included. Generally, the glycine-derived amides showed a higher activity than the β-alanine and GABA derivatives in the maximal electroshock seizure (MES) test in mice upon intraperitoneal administration. The activity was comparable to the respective taurine derivatives. The N,N-phthaloyl-glycine amides were also active in the MES test upon oral administration to rats. No significant activity was noted in the seizure threshold test with subcutaneous pentylene-tetrazole. The ED50 of N,N-phthaloyl-glycine ethyl amide (4b) in the MES test upon intraperitoneal administration to mice was 19.1 mg/kg. On a molar basis this activity is comparable to the activity of phenytoin with little toxicity in the rotorod test. In conclusion, N,N-phthaloyl-glycine amides might represent promising antiepileptic drugs.

Aminoalkyl-1,1-bis(phosphinic acids): Stability, acid-base, and coordination properties

Four geminal bis(phosphinic acids), namely, aminomethylbis(H-phosphinic acid) (H2L1) and 4-aminobutyl-1-hydroxy-1,1-bis(R-phosphinic acid) with R = H (H2L2), Me (H2L3) and CH2CH2COOH (H4L4), were studied. Their acid-base properties and coordination ability towards Cu2+, Ni2+ and Zn2+ ions were studied by potentiometry, UV/Vis spectroscopy and NMR spectroscopy. The amine group in H2L1 has a lower protonation constant (log Ka = 6.79) than those found for other studied bisphosphinates (log Ka = 10.75-11.05) with distant amine groups. The structure of [Ca(H2L2-O,O')(HL2-O,O')]Cl revealed an octahedral arrangement of the metal coordination sphere and a linear polymeric structure, which forms through eight-membered Ca(-O-P-O-)2Ca rings. The structure of [Cu(HL3-O,O')2(H2O)]·5H2O shows two chelating bisphosphinate groups in an equatorial O4 environment. The structure of [Cu(H0.5L3-O,O')(NO3)0.5]·2.25H2O shows two different coordination environments, one is an elongated tetragonal pyramid, and the other is a trigonal bipyramid with a bidentate nitrate ion. Four geminal bisphosphinates were synthesized, and their acid-base properties and coordination behaviour with Cu2+, Zn2+ and Ni2+ ions were studied. The compounds show lower amine basicity and complex stability constants than those of analogous bisphosphonates. In the solid-state structures of the Ca2+ and Cu2+ complexes, the bisphosphinates are coordinated in O,O'-chelating mode.

Carbonic anhydrase activators. Part 14. Syntheses of mono and bis pyridinium salt derivatives of 2-amino-5-(2-aminoethyl)- and 2-amino-5-(3-aminopropyl)-1,3,4-thiadiazole and their interaction with isozyme II

Reaction of 2-amino-5-(2-aminoethyl)- and 2-amino-5-(3-aminopropyl)-1,3,4-thiadiazole with 2,4,6-trisubstituted pyrylium salts in molar ratios of 1:1 and 1:2 afforded three series of derivatives which were investigated for their abilities to activate the enzyme carbonic anhydrase (CA). Only compounds possessing free aminoalkyl moieties behaved as strong CA II activators, presumably via a mechanism involving the shuttling of protons between the enzyme active site and the environment.

AMD070, a CXCR4 chemokine receptor antagonist: Practical large-scale laboratory synthesis

An efficient and convergent four-step synthetic route to the CXCR4 chemokine receptor antagonist AMD070 (1) has been developed which employs only a single chromatographic step in the entire sequence. Novel reductive amination methods have been developed for the coupling of 2 and 3 in which a dehydrative imine formation is followed by reduction with an attenuated borohydride reagent (zinc chloride and sodium borohydride). Selective extraction methods were employed to purify synthetic intermediates and remove reagents and impurities. A procedure has also been developed to isolate 1 in a pure crystalline form.

Amino acid derivatives. Part 6. Synthesis, in vitro antiviral activity and molecular docking study of new N-α-amino acid derivatives conjugated spacer phthalimide backbone

A series of phthalimido-(substituted-alkyl-2-thioureido)alkyl carboxylic acid derivatives 5–13 and methyl 2-(4-(phthalimido-2-yl)butanamido)alkyl carboxylates 14–23 were synthesized with the aim to develop newly non-nucleoside reverse transcriptase inhibi

Highly Stereoselective Synthesis of Isoindole Derivatives Containing an Azetidinone Ring

Isoindole derivatives containing an azetidin-2-one moiety were prepared from phthalic anhydride by an approach that involves a [2π+2π] cycloaddition of an imine to a novel ketene generated in situ, and an electrocyclic reaction of a zwitterionic intermediate. The reactions were highly stereoselective and trans-β-lactams were obtained as the sole observed products.

Amides of N-Deacetyllappaconitine and Amino Acids

Amides were prepared from N-deacetyllappaconitine and the amino acids glycine, taurine, and γ-aminobutyric acid.

α-Amino acid derived bisphosphonates. Synthesis and anti-resorptive activity

Eleven new bisphosphonates were prepared from naturally-occurring l-amino acids. The synthesis required special attention to amino and side-chain protections. The novel compounds were tested in TPTX (thyroparathyroidectomized) rats against arotinoid-induced hypercalcemia and were compared to alendronate. Most of the compounds showed moderate to no anti-resorptive activity. Two compounds were more active than clodronate, but less than alendronate. Limited SAR conclusions were drawn.