62965-10-0

Basic information

• Product Name: Cbz-L-tert-Leucine
• Synonyms: 2S-BenzyloxycarbonylaMino-3,3-diMethylbutyric Acid;3-Methyl-N-[(phenylMethoxy)carbonyl]-L-valine;Benzyloxycarbonyl-L-tert-leucine;N-(Benzyloxycarbonyl)-L-tert-butylglycine;N-Benzyloxycarbonyl-tert-leucine;N-Carbobenzoxy-(S)-tert-leucine;(S)-2-(((Benzyloxy)carbonyl)aMino)-3,3-diMethylbutanoic acid;(2S)-2-([(Benzyloxy)Carbonyl]AMino)-3,3-DiMethylbutanoic Acid DicyclohexylaMine Salt
• CAS NO: 62965-10-0
• Molecular Formula: C₁₄H₁₉NO₄
• Molecular Weight: 265.3
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Amino Acid Derivatives;Leucine [Leu, L];Amino Acids & Deriv.;CHIRAL CHEMICALS;Amino Acids & Derivatives
• Mol File: 62965-10-0.mol

Chemical Properties

• Boiling Point: 436.4 ºC at 760 mmHg
• Flash Point: 217.7 ºC
• Appearance: White powder
• Density: 1.16 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.528
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 4.01±0.10(Predicted)
• CAS DataBase Reference: Cbz-L-tert-Leucine(CAS DataBase Reference)
• NIST Chemistry Reference: Cbz-L-tert-Leucine(62965-10-0)
• EPA Substance Registry System: Cbz-L-tert-Leucine(62965-10-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 62965-10-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Cbz-L-tert-Leucine is used as a building block for the synthesis of TRPV4 antagonists, which are potential therapeutic agents for the treatment of various diseases, including cystic fibrosis, chronic obstructive pulmonary disease (COPD), and heart failure. The Cbz group provides temporary protection to the amino group during the synthesis process, ensuring the correct formation of the desired compound.
Cbz-L-tert-Leucine is also used as a precursor in the development of HIV-1 protease inhibitors. These inhibitors are crucial in the treatment of HIV/AIDS, as they block the activity of the HIV-1 protease enzyme, preventing the virus from replicating and spreading in the body. The Cbz group aids in the synthesis of these inhibitors, ensuring the correct formation and stability of the final product.
Furthermore, Cbz-L-tert-Leucine serves as a key component in the synthesis of serine protease inhibitors. These inhibitors are valuable in the treatment of various conditions, such as inflammation, coagulation disorders, and cancer. The Cbz group plays a crucial role in the synthesis process, providing the necessary protection to the amino group and facilitating the formation of the desired serine protease inhibitor.

InChI:InChI=1/C14H19NO4/c1-14(2,3)11(12(16)17)15-13(18)19-9-10-7-5-4-6-8-10/h4-8,11H,9H2,1-3H3,(H,15,18)(H,16,17)/t11-/m1/s1

Upstream product

• 20859-02-3 L-tert-Leucine 
• 501-53-1 benzyl chloroformate 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 621-84-1 O-benzyl carbamate 
• 13795-24-9 benzyl 4-nitrophenyl carbonate 
• 100-51-6 benzyl alcohol 
• 62965-37-1 (S)-2-(((benzyloxy)carbonyl)amino)-3,3-dimethylbutanoic acid dicyclohexylammonium salt 
• 62965-57-5 (±)-2-amino-3,3-dimethylbutanamide 
• 68222-59-3 2(S)-{(benzyloxycarbonyl)amino}-3,3-dimethylbutanoic acid 

Downstream Products

• 68222-60-6 benzyloxycarbonyl-L-tert-leucyl-L-valine methyl ester 
• 848777-16-2 benzyl N-[(1S)-1-(hydroxymethyl)-2,2-dimethyl-propyl]carbamate 
• 609367-72-8 [(S)-2,2-Dimethyl-1-(pyrrolidine-1-carbonyl)-propyl]-carbamic acid benzyl ester 
• 609367-74-0 [(S)-2,2-Dimethyl-1-(4-methyl-piperazine-1-carbonyl)-propyl]-carbamic acid benzyl ester 
• 325459-64-1 2S-[1-(4-benzyl-piperidine-1-carbonyl)-2,2-dimethyl-propyl]-carbamic acid benzyl ester 
• 609367-76-2 [(S)-1-(4-Acetyl-piperidine-1-carbonyl)-2,2-dimethyl-propyl]-carbamic acid benzyl ester 
• 854055-62-2 Z-L-Tle-Aib-OtBu 
• 872983-55-6 [(1S)-1-((1S)-1-{1-benzylcarbamoyl-1-[2-(tert-butyldiphenylsiloxy)ethyl]butylcarbamoyl}-2-phenylethylcarbamoyl)-2,2-dimethylpropyl]carbamic acid benzyl ester 
• 872983-60-3 [(1S)-1-((1S)-1-{1-benzylcarbamoyl-1-[2-(tert-butyldiphenylsiloxy)ethyl]butylcarbamoyl}-3-dimethylamino-3-oxopropylcarbamoyl)-2,2-dimethylpropyl]carbamic acid benzyl ester 
• 872983-68-1 [(1S)-1-((1S)-1-{1-benzylcarbamoyl-1-[2-(tert-butyldiphenylsiloxy)ethyl]-3-methylbutylcarbamoyl}-3-dimethylamino-3-oxopropylcarbamoyl)-2,2-dimethylpropyl]carbamic acid benzyl ester 
• 325796-51-8 [1S-(4-Hydroxy-piperidine-1-carbonyl)-2,2-dimethyl-propyl]-carbamic acid benzyl ester 
• 159006-10-7 phenylmethyl [1S-[[[2R-hydroxy-3-[(3-methylbutyl) (phenylsulfonyl)amino]-1S-(phenylmethyl)propyl]amino] carbonyl]-2,2-dimethylpropyl]carbamate 
• 169437-02-9 2S-[[(dimethylamino)acetyl]amino]-N-[2R-hydroxy-3-[(3-methyl-butyl)(phenylsulfonyl)amino]-1S-(phenylmethyl)propyl]-3,3-dimethylbutaneamide 
• 159006-07-2 2S-[[(dimethylamino)acetyl]amino]-N-[2R-hydroxy-3-[(3-methylbutyl) (methylsulfonyl)amino]-1S-(phenylmethyl)propyl]-3,3-dimethylbutanamide 

Relevant articles and documents

Optimization of peptide-based inhibitors targeting the HtrA serine protease in Chlamydia: Design, synthesis and biological evaluation of pyridone-based and N-Capping group-modified analogues

The obligate intracellular bacterium Chlamydia trachomatis (C. trachomatis) is responsible for the most common bacterial sexually transmitted infection and is the leading cause of preventable blindness, representing a major global health burden. While C.

Amino acid chiral ligand containing bidentate coordination group, chiral catalyst, and corresponding preparation methods and applications thereof

The present invention relates to an amino acid chiral ligand containing a bidentate coordination group, a chiral catalyst, and corresponding preparation methods and applications thereof. The chiral ligand is prepared from a cheap and easily available amino acid, and the development of the chiral ligand can improve the diversity of the chiral ligand. The chiral Ir (III) catalyst is simply and efficiently prepared from the chiral ligand only through a one-step reaction. The chiral Ir (III) catalyst is characterized in that a bidentate guiding group is introduced to an amino acid framework to change the original coordination mode of the amino acid and Ir in order to enhance the chiral control ability of the amino acid to the Ir(III) catalyst. The chiral Ir(III) catalyst is designed and synthesized for the first time, and the selectivity reaches up to 99% ee when the catalyst is successfully applied to the high-efficiency asymmetric synthesis of chiral gamma-cyclolactam, so the catalyst has superior stereo control ability.

Prodrug of an ice inhibitor

This invention describes an ICE inhibitor prodrug (I) having good bioavailability. Compound I is useful for treating IL-1 mediated diseases such as rheumatoid arthritis, inflammatory bowel disease, Crohn's disease, ulcerative colitis, inflammatory periton

Bifunctional Br?nsted Base Catalyzes Direct Asymmetric Aldol Reaction of α-Keto Amides

The first enantioselective direct cross-aldol reaction of α-keto amides with aldehydes, mediated by a bifunctional ureidopeptide-based Br?nsted base catalyst, is described. The appropriate combination of a tertiary amine base and an aminal, and urea hydro

PEPTIDOMIMETIC COMPOUNDS AND ANTIBODY-DRUG CONJUGATES THEREOF

This invention relates to peptidomimetic linkers and anti-body drug conjugates thereof, to pharmaceutical compositions containing them, and to their use in therapy for the prevention or treatment of cancer.

Ureidopeptide-based Bronsted bases: Design, synthesis and application to the catalytic enantioselective synthesis of β-amino nitriles from (arylsulfonyl)acetonitriles

The addition of cyanoalkyl moieties to imines is a very attractive method for the preparation of β-amino nitriles. We present a highly efficient organocatalytic methodology for the stereoselective synthesis of β-amino nitriles, in which the key to success is the use of ureidopeptide-based Bronsted base catalysts in combination with (arylsulfonyl)acetonitriles as synthetic equivalents of the acetonitrile anion. The method gives access to a variety of β-amino nitriles with good yields and excellent enantioselectivities, and broadens the stereoselective Mannich-type methodologies available for their synthesis. Learning from peptides: A concise route for the catalytic enantioselective synthesis of β-amino nitriles has been achieved by using ureidopeptide-based Bronsted bases as catalysts in the Mannich reaction of N-Boc imines and (arylsulfonyl)acetonitriles (see scheme; Boc=tert-butoxycarbonyl, napht=naphthyl, TMS=trimethylsilyl).

IAP ANTAGONISTS

There are disclosed compounds that modulate the activity of inhibitors of apoptosis (IAPs), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders and disorders of dysregulated apoptosis, such as cancer, utilizing the compounds of the invention.

PROCESS FOR PRODUCTION OF N-ALKOXYCARBONYL-tert-LEUCINES

A high quality N-alcoxycarbonyl-tert leucine can be efficiently and stably produced with an easy procedure by reacting tert-leucine with an N-alcoxycarbonylating agent in the presence of water, wherein the use amount of the N-alcoxycarbonylating agent is not less than 0.90 times by mole and not more than 1.00 times by mole relative to the tert-leucine, with maintaining the pH of the reaction mixture in the range of not less than 9 and not more than 13 using a basic agent. In addition, an N-alcoxycarbonyl-tert-leucine can be efficiently extracted from the basic aqueous solution thereof under a mild condition using a water-immiscible solvent by mixing a hydroxide. Furthermore, the two crystal forms of N-butoxycarbonyl-tert-leucine can be controlled by adjusting the water amount in crystallization step, and the compound can be stably produced in an industrial production.

PROCESS FOR THE PREPARATION OF PROTEASE INHIBITORS

A process for preparing enantioselectively a compound of formula (la) or (Ib) over a compound of formulas I-2—1h.

PROCESSES AND INTERMEDIATES

A process for preparing enantioselectively a compound of formula la or lb: over a compound of formulas 1-2 - Ih: