102123-74-0

Basic information

• Product Name: (3S)-3-(tert-Butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone
• Synonyms: Carbamic acid,N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-, 1,1-dimethylethyl ester;(3S)-3-(N-Boc-amino)-1-chloro-4-phenyl-2-butanone;(3S)-3-(tert-Butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone;Carbamic acid, [(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-, 1,1-dimethylethyl ester (9CI);N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-Carbamic acid 1,1-dimethylethyl ester;N-[(1S)-3-chloro-2-oxo-1-(phenylMethyl)propyl]-;(S)-tert-Butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbaMate
• CAS NO: 102123-74-0
• Molecular Formula: C₁₅H₂₀ClNO₃
• Molecular Weight: 297.78
• EINECS: 1312995-182-4
• Mol File: 102123-74-0.mol

Chemical Properties

• Melting Point: 103 °C
• Boiling Point: 423.882 °C at 760 mmHg
• Flash Point: 210.157 °C
• Appearance: /
• Density: 1.15 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.517
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 10.94±0.46(Predicted)
• CAS DataBase Reference: (3S)-3-(tert-Butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-3-(tert-Butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone(102123-74-0)
• EPA Substance Registry System: (3S)-3-(tert-Butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone(102123-74-0)

Safety Data

• Hazardous Substances Data: 102123-74-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(3S)-3-(tert-Butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone is utilized as a building block in organic synthesis for the creation of more complex molecules. Its unique structural features make it a valuable component in the synthesis of various organic compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (3S)-3-(tert-Butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone serves as a starting material for the preparation of pharmaceuticals and bioactive compounds. Its structural characteristics allow for the development of new drugs with potential therapeutic applications.
Used in Pharmaceutical Research:
(3S)-3-(tert-Butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone is also employed in pharmaceutical research as a starting material for the synthesis of various compounds with potential medicinal properties. Its unique structure and reactivity contribute to the discovery and development of new therapeutic agents.
Used in Drug Development:
Due to its structural features, (3S)-3-(tert-Butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone may have potential pharmaceutical applications. It can be further modified and optimized to develop new drugs with improved efficacy and selectivity for specific targets in the treatment of various diseases.

InChI:InChI=1/C15H20ClNO3/c1-15(2,3)20-14(19)17-12(13(18)10-16)9-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,17,19)/t12-/m0/s1

Upstream product

• 120238-42-8 methyl (S)-2-(diphenylmethylideneamino)-3-phenylpropanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 34351-19-4 (3S)-3-amino-1-chloro-4-phenyl-2-butanone hydrochloride 
• 186581-53-3 diazomethane 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 85613-64-5 (S)-3-(tert-butoxycarbonyl)amino-4-phenyl-2-butanone 
• 119153-87-6 (C₅H₉O₂)C₉H₉NO(O)(CO₂C₂H₅) 
• 910642-68-1 C₁₅H₂₀N₃O₃⁽¹⁺⁾ 
• 290836-37-2 (3S)-3-tert-butoxycarbonylamino-1,1-dichloro-4-phenyl-2-butanone 
• 67729-36-6 Boc-Phe-O-COO-isoBu 
• 286019-77-0 (3S)-1-chloro-3-(diphenylmethylene)amino-4-phenyl-2-butanone 
• 339190-43-1 N-benzylidene (S)-phenylalanine methyl ester 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 7535-56-0 N-t-butoxycarbonyl-L-phenylalanine 4-nitrophenyl ester 

Downstream Products

• 162536-40-5 (2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane 
• 155847-91-9 [(S)-1-((S)-1-Benzyl-3-chloro-2-oxo-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 155650-95-6 3,6-dibenzyl-5-methylpyrazin-2(1H)-one 
• 155847-96-4 6-Benzyl-5-methyl-1H-pyrazin-2-one 
• 35172-58-8 [((S)-1-Benzyl-3-chloro-2-oxo-propylcarbamoyl)-methyl]-carbamic acid tert-butyl ester 
• 169280-56-2 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide 
• 206361-99-1 darunavir 
• 160232-08-6 (2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol 
• 191226-98-9 [(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester 
• 165727-45-7 tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate 
• 162539-71-1 {(1S,2R)-1-Benzyl-3-[((S)-3-tert-butoxycarbonylamino-2-oxo-4-phenyl-butyl)-methyl-amino]-2-hydroxy-propyl}-carbamic acid tert-butyl ester 
• 152438-66-9 Boc-Phe-4-acetylphenoxymethyl ketone 
• 794525-88-5 {1S-benzyl-2R-(tert-butyldimethylsilanyloxy)-4R-[1-(1S-carbamoyl-2-phenyl-ethylcarbamoyl)-3-(1S)-methyl-butylcarbamoyl]-5-[4-(2-phenyl-[1.3]dioxolan-2-yl)phenyl]-pentyl}carbamic acid tert-butyl ester 
• 794525-90-9 {1S-benzyl-4R-[1-(1S-carbamoyl-2-phenyl-ethylcarbamoyl)-3-(1S)-methyl-butylcarbamoyl]-2R-hydroxy-5-[4-(2-phenyl-[1.3]dioxolan-2-yl)phenyl]-pentyl}carbamic acid tert-butyl ester 

Relevant articles and documents

Design and Optimization of a Continuous Stirred Tank Reactor Cascade for Membrane-Based Diazomethane Production: Synthesis of α-Chloroketones

The development of a continuous diazomethane generator comprising a continuous stirred tank reactor (CSTR) cascade and membrane separation technology is reported. This reactor concept was applied for the telescoped three-step synthesis of a chiral α-chloroketone, a key building block for many HIV protease inhibitors, via a modified Arndt-Eistert reaction starting from N-protected l-phenylalanine. The initial mixed anhydride was generated in a coil reactor and directly introduced into the CSTR diazomethane cascade. The use of a semipermeable Teflon membrane (AF-2400) allowed the generation of anhydrous diazomethane, which diffuses through the membrane into the CSTR where it is immediately consumed by the anhydride to furnish the corresponding diazoketone. The subsequent halogenation with concentrated HCl was performed downstream in batch and allowed production of the α-chloroketone on a multigram scale, with a productivity of 1.54 g/h (5.2 mmol/h).

A practical method for the preparation of α'-chloroketones of N-carbanaate protected-α-aminoacids

A practical method for the preparation of α-N-BOC-epoxides from protected amino acid esters based on the Kowalski homologation reaction is described. This procedure can be readily performed on a large scale without the use of hazardous reagents and has allowed preparation of epoxides 3 in multi-kilogram quantities.

Practical synthesis of α-aminoalkyl-α′-chloromethylketone derivatives. Part 2: Chloromethylation of N-imine-protected amino acid esters

Chloromethylation of N-imine-protected amino acid esters followed by acid hydrolysis gave α-aminoalkyl-α′-chloromethylketone as a HCl salt form in good yield without racemization. The amino group was conveniently protected with carbamate protecting reagents to give various useful intermediates for the protease inhibitors.

Synthesis method of (2S, 3S)-3-(t-butyloxycarboryl amino)-1, 2-epoxy-4-phenylbutane

The invention relates to the technical field of synthesis of drug intermediates, in particular to a synthesis method of (2S, 3S)-3-(t-butyloxycarboryl amino)-1, 2-epoxy-4-phenylbutane. The method comprises the following steps: condensing N-t-butyloxycarboryl-L-phenylalanine serving as a raw material with substituted phenol under the action of a condensing agent to obtain active ester 15; reacting the active ester 15 with a ylide reagent and alkali to obtain a sulfoxide ylide intermediate 16; reacting the sulfoxide ylide intermediate 16 with halide salt under the action of a catalyst to obtain a halogenated ketone intermediate 6; reducing the halogenated ketone intermediate 6 through a reducing agent under the action of a catalyst to obtain a halogenated methanol intermediate 7; and removing halogen acid from the halogenated methanol intermediate 7 under the action of alkali, and carrying out condensation cyclization to obtain the target product (2S, 3S)-3-(t-butyloxycarboryl amino)-1, 2-epoxy-4-phenylbutane. The synthesis method of the (2S, 3S)-3-(t-butyloxycarboryl amino)-1, 2-epoxy-4-phenylbutane, provided by the invention, has the characteristics of cheap and easily available initial raw materials, safe and controllable process and easiness in operation.

SULFOXONIUM YLIDE DERIVATIVES AS PROBES FOR CYSTEINE PROTEASE

The present invention relates to compounds of formula I bearing a sulfoxonium ylide moiety as warhead, or salts thereof. Such compounds can be used as activity-based probes for cysteine proteases such as cathepsin X, in methods of detecting cysteine protease activity and in related diagnostic or therapeutic methods.

A process for the preparation method of the sulfuric acid [...] intermediates

The invention discloses a method for preparing sulfuric acid [...] intermediate (2 R, 3 S) - 1, 2 - epoxy - 3 - tert-butoxycarbonyl amino - 4 - phenyl butane of the method, the method cheap L - phenylalanine as the starting material, by with the di-T-n-butyl reaction for protecting amino group, with acetic anhydride condensation, with hydrochloric acid after the occurrence of the chloro in the chiral catalyst under the effects of the asymmetric hydrogenation reduction, finally cyclization under basic conditions to obtain the target product. The present invention provides of sulfuric acid is an important intermediate [...] (2 R, 3 S) - 1, 2 - epoxy - 3 - tert-butoxycarbonyl amino - 4 - phenyl butane preparation method of the raw material is cheap, mild reaction conditions, the synthesis efficiency is high, it is suitable for industrial production, in order to prepare sulfuric acid [...] and intermediate provides a highly efficient way.

4-amino-N-[ (2R, 3S) - 3-amino-2-hydroxy-4-phenyl-butyl]-N- isobutyl-benzene sulfonaide preparation method

The invention discloses a method for preparing 4-amino-N-[(2R,3S)-3-amino-2-hydroxy-4-benzene butyl]-N-isobutyl benzsulfamide. The method comprises the following steps: S1: enabling L-phenylalanine and diazomethane to react to obtain a diazo methyl ketone intermediate product, and enabling the diazo methyl ketone intermediate product and haloid acid to react to obtain a compound A; S2, conducting carbonyl deoxidation on the compound A to obtain a compound B; S3, under the existence of iso-butylamine, conducting cyclization reaction and ring-opening reaction on the compound B in sequence to obtain a compound C; S4, enabling the compound C and nitrobenzenesulfonyl chloride to react to obtain a compound D; S5, conducting nitro reduction on the compound D to obtain the 4-amino-N-[(2R,3S)-3-amino-2-hydroxy-4-benzene butyl]-N-isobutyl benzsulfamide. The method is simple in course, low in cost, mild in condition, and higher in intermediate product stability, and is beneficial for industrial application.

METHOD FOR THE PREPARATION OF DIAZOALKANES

The present invention relates to a method of forming diazoalkanes. One aspect of the present invention provides a method for the production of a N-alkyl-N-nitroso compound from a starting material, comprising the use of a tribasic acid to acidify an amine. A second aspect of the present invention provides a method for the production of a diazoalkane, comprising reacting a N-alkyl-N-nitroso compound with a base and a phase transfer catalyst, wherein no organic solvent is used.

Continuous flow synthesis of α-halo ketones: Essential building blocks of antiretroviral agents

The development of a continuous flow process for the multistep synthesis of α-halo ketones starting from N-protected amino acids is described. The obtained α-halo ketones are chiral building blocks for the synthesis of HIV protease inhibitors, such as atazanavir and darunavir. The synthesis starts with the formation of a mixed anhydride in a first tubular reactor. The anhydride is subsequently combined with anhydrous diazomethane in a tube-in-tube reactor. The tube-in-tube reactor consists of an inner tube, made from a gas-permeable, hydrophobic material, enclosed in a thick-walled, impermeable outer tube. Diazomethane is generated in the inner tube in an aqueous medium, and anhydrous diazomethane subsequently diffuses through the permeable membrane into the outer chamber. The α-diazo ketone is produced from the mixed anhydride and diazomethane in the outer chamber, and the resulting diazo ketone is finally converted to the halo ketone with anhydrous ethereal hydrogen halide. This method eliminates the need to store, transport, or handle diazomethane and produces α-halo ketone building blocks in a multistep system without racemization in excellent yields. A fully continuous process allowed the synthesis of 1.84 g of α-chloro ketone from the respective N-protected amino acid within ～4.5 h (87% yield).

CRYSTALLINE DARUNAVIR

The present invention relates to a non-solvated crystalline Darunavir, process for its preparation and pharmaceutical composition comprising it. The present invention also relates to a process for the preparation of amorphous Darunavir from a non-solvated crystalline Darunavir.