135042-12-5

Basic information

• Product Name: (2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid
• Synonyms: (2R,4R)-N-ALPHA-T-BUTOXYCARBONYL-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID;BOC-(2R,4R)-(+)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID;BOC-CIS-4-HYDROXY-D-PROLINE;BOC-D-CISHYP-OH;N-T-BOC-CIS-4-HYDROXY-D-PROLINE;N-BOC-CIS-4-HYDROXY-D-PROLINE;N-ALPHA-BUTOXYCARBONYL-CIS-4-HYDROXY-D-PROLINE;(2r,4r)-n-boc-4-hydroxypyrrolidine-2-carboxylic acid
• CAS NO: 135042-12-5
• Molecular Formula: C₁₀H₁₇NO₅
• Molecular Weight: 231.25
• EINECS: 1312995-182-4
• Mol File: 135042-12-5.mol

Chemical Properties

• Melting Point: 145°C
• Boiling Point: 390.9 °C at 760 mmHg
• Flash Point: 190.2 °C
• Appearance: /
• Density: 1.312
• Vapor Pressure: 9.99E-08mmHg at 25°C
• Refractive Index: 1.531
• Storage Temp.: 2-8°C
• PKA: 3.80±0.40(Predicted)
• CAS DataBase Reference: (2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid(135042-12-5)
• EPA Substance Registry System: (2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid(135042-12-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 135042-12-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid is used as a starting material for the synthesis of DNA mimicking pyrrolidine peptide nucleic acid (PNA) analogs. These PNA analogs have potential applications in the development of new drugs for gene regulation and targeted therapies.
Used in Organic Synthesis:
(2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid is used as an intermediate in the synthesis of biologically important macrocyclic dilactones. These macrocyclic compounds have various applications in the pharmaceutical and chemical industries, including as potential drug candidates and in the development of new materials.
Used in Medicinal Chemistry:
(2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid is used as an intermediate in the synthesis of histamine H3 receptor antagonists. These antagonists have potential therapeutic applications in the treatment of various conditions, such as cognitive disorders, sleep-wake regulation, and allergic responses.

InChI:InChI=1/C10H17NO5/c1-10(2,3)16-9(15)11-5-6(12)4-7(11)8(13)14/h6-7,12H,4-5H2,1-3H3,(H,13,14)/t6-,7-/m1/s1

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 2584-71-6 cis-hydroxy-D-proline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 77450-00-1 (2R,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester 
• 295365-33-2 ethyl tert-butoxycarbonylamino(toluene-4-sulfonyl)acetate 
• 502442-65-1 ethyl (2R,4R)-N-tert-butyloxycarbonyl-4-tert-butyldiphenylsiloxyprolinate 
• 502442-54-8 ethyl (4R)-2-(N-tert-butyloxycarbonylamino)-4,5-dihydroxy-2-pentenoa 
• 77449-94-6 (2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride 
• 441067-49-8 (2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride 
• 34619-03-9 tert-butyldicarbonate 
• 114676-69-6 (2R,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate 
• 51-35-4 4R-4-hydroxyproline 
• 502442-59-3 ethyl (4R)-2-(N-tert-butyloxycarbonylamino)-5-tert-butyldimethylsiloxy-4-tert-butyldiphenylsiloxy-2-pentenoate 

Downstream Products

• 114676-69-6 (2R,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate 
• 189163-46-0 1-(1,1-dimethylethyl) 2-(diphenylmethyl) (2R,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 198969-16-3 (2R,4R)-4-Benzyloxy-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester 
• 158459-11-1 cis-4-benzyloxy-N-tert-butoxycarbonyl-D-proline 
• 2584-71-6 cis-hydroxy-D-proline 
• 906536-17-2 (2R,4R)-1-(tert-butoxycarbonyl)-4-(naphthalen-2-ylmethoxy)pyrrolidine-2-carboxylic acid 
• 474023-61-5 (R)-2-amino-1-((2S,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-3-phenylpropan-1-one 
• 906536-59-2 N-((R)-1-((2S,4R)-2-(3-aminopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)acetamide 
• 906536-51-4 N-((R)-1-((2S,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)acetamide 
• 474023-60-4 tert-butyl (R)-1-((2S,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate 
• 906536-85-4 tert-butyl (R)-1-((2S,4R)-2-(3-aminopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate 
• 906536-18-3 tert-butyl (2R,4R)-2-(2-(benzyloxycarbonylamino)ethylcarbamoyl)-4-(naphthalen-2-ylmethoxy)pyrrolidine-1-carboxylate 
• 906536-58-1 N-((R)-1-((2S,4R)-2-(3-aminopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)-3-phenylpropanamide 
• 906536-50-3 N-((R)-1-((2S,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)-3-phenylpropanamide 

Relevant articles and documents

Oxy-peptide nucleic acid with a pyrrolidine ring that is configurationally optimized for hybridization with DNA

Four stereoisomers of oxy-peptide nucleic acids containing ether linkages in the main chain and conformationally-restricted pyrrolidine rings (pyrrolidine-based oxy-PNA = POPNA) were newly synthesized and investigated for binding to DNA. cis-L-POPNA with 9 adenine bases formed the most stable hybrid with dT9. The POPNA showed high sequence specificity similar to that of the Nielsen-type PNA and sharper melting behavior in hybridization with DNA than the Nielsen-type PNA.

Discovery of Potent and Orally Bioavailable Dihydropyrazole GPR40 Agonists

G protein-coupled receptor 40 (GPR40) has become an attractive target for the treatment of diabetes since it was shown clinically to promote glucose-stimulated insulin secretion. Herein, we report our efforts to develop highly selective and potent GPR40 agonists with a dual mechanism of action, promoting both glucose-dependent insulin and incretin secretion. Employing strategies to increase polarity and the ratio of sp3/sp2 character of the chemotype, we identified BMS-986118 (compound 4), which showed potent and selective GPR40 agonist activity in vitro. In vivo, compound 4 demonstrated insulinotropic efficacy and GLP-1 secretory effects resulting in improved glucose control in acute animal models.

HUMAN PLASMA KALLIKREIN INHIBITORS

Disclosed are compounds of formula I, and pharmaceutically acceptable salts thereof. The compounds are inhibitors of plasma kallikrein. Also provided are pharmaceutical compositions comprising at least one compound of the invention, and methods involving use of the compounds and compositions of the invention in the treatment and prevention of diseases and conditions characterized by unwanted plasma kallikrein activity.

Amino 6-membered ring derivative and pharmaceutical applications thereof including the use for manufacturing dipeptidyl peptidase-4(IDPP-IV) inhibitor

The present invention relates to an amino 6-membered ring derivative and pharmaceutical applications thereof, which specifically relates to the amino 6-membered ring derivative represented by the general formula (I) or stereoisomers thereof, pharmaceutically acceptable salts thereof, a prodrug, a pharmaceutical composition comprising the derivative, and the pharmaceutical use for manufacturing dipeptidyl peptidase-4(IDPP-IV) inhibitor, wherein the definition of each substituent in the general formula (I) is the same as described in the specification.

Propargyloxyproline Regio- and Stereoisomers for Click-Conjugation of Peptides: Synthesis and Application in Linear and Cyclic Peptides

The use of the click reaction for the introduction of conjugate groups, such as affinity or fluorescent labels, to a peptide for the study of peptide biochemistry and pharmacology is widespread. However, the nature and location of substituted 1,2,3-triazoles in peptide sequences may markedly affect conformation or binding as compared with native sequences. We have examined the preparation and application of propargyloxyproline (Pop) residues as a precursor to such peptide conjugates. Pop residues are available in a range of regio- and stereoisomers from hydroxyproline precursors and are readily prepared in Fmoc-protected form. They can be incorporated routinely in peptide synthesis and broadly retain the conformational properties of the parent proline containing peptides. This is exemplified by the preparation of biotin- and fluorophore-labelled peptides derived from linear and cyclic peptides.

HETEROCYCLIC COMPOUND

An object of the present invention is to provide a compound having a superior CH24H inhibitory action, which is useful as an agent for the prophylaxis or treatment of epilepsy, neurodegenerative disease and the like. The present invention relates to a compound represented by the formula: wherein each symbol is as defined in the specification, or a salt thereof.

Direct asymmetric aldol reactions catalysed by trans-4-hydroxy-(S)-prolinamide in solvent-free conditions

Direct asymmetric aldol reactions between 4-nitrobenzaldehyde and cyclohexanone were catalysed by trans-4-hydroxy-(S)-prolinamide (10 mol %) in the presence of CH3COOH (10 mol %) as the co-catalyst under solvent-free conditions at 15 °C. (2S,4R)-4-Hydroxy-N-((S)-1-phenylethyl)pyrrolidine-2-carboxamide 2 efficiently catalysed the asymmetric aldol reaction to afford the product in >99% yield and with 95% ee with an anti/syn ratio of 88:12 after 18 h. The additional trans-hydroxyl group on (S)-prolinamide and (S)-1-phenylethylamine both influenced the ee of the predominant anti aldol product. Different benzaldehyde derivatives with cyclohexanone gave the corresponding aldol products in 38-89% yields and with 56-94% ee with anti/syn (100:0-71:29). Catalyst 2 can be used up to 5 continuous cycles for asymmetric aldol reactions between 4-nitrobenzaldehyde and cyclohexanone with overall 91% yield and 86% yield of anti-product with anti/syn (98:2).

PYRROLIDINE GPR40 MODULATORS

The present invention provides compounds of Formula (I): or a stereoisomer, or a pharmaceutically acceptable salt thereof, wherein all of the variables are as defined herein. These compounds are GPR40 G protein-coupled receptor modulators which may be used as medicaments.

6H-IMIDAZO[1,5-a]PYRROLO[2,3-e]PYRAZINE COMPOUNDS

The invention provides a compound of Formula (I as defined herein, pharmaceutically acceptable salts, pro-drugs, biologically active metabolites, stereoisomers and isomers thereof wherein the variables are defined herein. The compounds of the invention are useful for treating immunological and oncological conditions.

6H-IMIDAZO[1,5-a]PYRROLO[2,3-e]PYRAZINE COMPOUNDS

The invention provides a compound of Formula (I) as defined herein, pharmaceutically acceptable salts, pro-drugs, biologically active metabolites, stereoisomers and isomers thereof wherein the variables are defined herein. The compounds of the invention are useful for treating immunological and oncological conditions.