182210-00-0

Basic information

• Product Name: (+)-N-CARBOBENZYLOXY-D-PROLINE METHYL ESTER
• Synonyms: (+)-N-CARBOBENZYLOXY-D-PROLINE METHYL ESTER;D-ZPROME;R-1-CBZ-PYRROLIDINE-2-CARBOXYLIC ACID METHYL ESTER;CB2-D-Pro-OME;(R)-1-Benzyl 2-Methyl pyrrolidine-1,2-dicarboxylate
• CAS NO: 182210-00-0
• Molecular Formula: C₁₄H₁₇NO₄
• Molecular Weight: 263.29
• Mol File: 182210-00-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (+)-N-CARBOBENZYLOXY-D-PROLINE METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-N-CARBOBENZYLOXY-D-PROLINE METHYL ESTER(182210-00-0)
• EPA Substance Registry System: (+)-N-CARBOBENZYLOXY-D-PROLINE METHYL ESTER(182210-00-0)

Safety Data

• Hazardous Substances Data: 182210-00-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(+)-N-CARBOBENZYLOXY-D-PROLINE METHYL ESTER is used as a key intermediate in organic synthesis for the preparation of various complex organic molecules. Its unique structure allows for selective reactions and the formation of desired products with high yields.
Used in Pharmaceutical Production:
In the pharmaceutical industry, (+)-N-CARBOBENZYLOXY-D-PROLINE METHYL ESTER is used as a building block for the synthesis of biologically active molecules and drug candidates. Its versatility and the presence of the N-CARBOBENZYLOXY protecting group make it an ideal component for the development of new drugs with potential therapeutic applications.
Used in Peptide Synthesis:
(+)-N-CARBOBENZYLOXY-D-PROLINE METHYL ESTER is employed as a protected amino acid in peptide synthesis. The N-CARBOBENZYLOXY group temporarily masks the amine functionality, preventing unwanted side reactions and allowing for the stepwise assembly of peptide chains with high precision and yield.
Used in Research and Development:
In research settings, (+)-N-CARBOBENZYLOXY-D-PROLINE METHYL ESTER is utilized for the investigation of new synthetic methods, the development of novel drug candidates, and the study of biologically active molecules. Its unique properties make it a valuable tool for advancing scientific knowledge and discovering new applications in the field of chemistry and drug development.

Upstream product

• 344-25-2 D-Prolin 
• 67-56-1 methanol 
• 61350-62-7 N-benzyloxycarbonyl-D-proline acid chloride 
• 6404-31-5 Z-D-proline 
• 182005-26-1 (R)-2-benzyloxycarbonylamino-5-hydroxypentanoic acid methyl ester 
• 26566-11-0 N-(benzyloxycarbonyl)-D-glutamic acid 1-methyl ester 
• 501-53-1 benzyl chloroformate 
• 108645-62-1 N-benzyloxycarbonylproline methyl ester 
• 182005-31-8 (R)-2-Benzyloxycarbonylamino-5-bromo-pentanoic acid methyl ester 
• 1148-11-4 N-carbobenzyloxyproline 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 947300-02-9 (R)-2-(2-cyanoacetyl)pyrrolidine-1-benzyl formate 
• 1350723-65-7 (R)-2-(5-amino-1-methyl-1H-pyrazol-3-yl)pyrrolidine-1-benzyl formate 
• 1350723-66-8 (R)-2-(5-amino-4-cyclohexenyl-1-methyl-1H-pyrazol-3-yl)pyrrolidine-1-benzyl formate 
• 1140496-82-7 C₁₆H₂₂NO₆P 
• 108855-11-4 Z-L-Phe-D-prolinal 
• 108807-54-1 Z-D-prolinal semicarbazone 
• 259868-53-6 methyl (R)-3-(1-{2-[tris-(4-methoxyphenyl)methoxy]ethyl}pyrrolidin-2-yl)propionate 
• 259868-49-0 methyl (R)-3-[1-(4,4-diphenylbut-3-en-1-yl)pyrrolidin-2-yl]propionate 
• 259868-85-4 methyl (R)-3-[1-(benzyloxycarbonyl)pyrrolidin-2-yl]acrylate 
• 323183-51-3 (2R)-N-({(3R)-1-(tert-butoxycarbonyl)-3-piperidyl)methyl)-1-{(2S,4R)-4-(tert-butoxy)-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl}-carbonylpyrrolidine-2-carboxamide 
• 323182-20-3 (2R)-1-{(2S,4R)-4-hydroxy-1-(3,3,3-triphenylpropanoyl)-pyrrolidin-2-yl}carbonyl-N-((3S)-3-piperidylmethyl)pyrrolidine-2-carboxamide 
• 545380-40-3 (R)-1-[(2S,4R)-4-tert-Butoxy-1-(3,3,3-triphenyl-propionyl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carboxylic acid methyl ester 
• 323183-79-5 (2R)-1-{(2S,4R)-4-(tert-butoxy)-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl}carbonylpyrrolidine-2-carboxylic acid 
• 545380-39-0 methyl (2R)-1-([(2S,4R)-4-tert-butoxy-1-(benzyloxycarbonyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carboxylate 

Relevant articles and documents

Identification of novel muscarinic M(3) selective antagonists with a conformationally restricted Hyp-Pro spacer.

The identification of potent and selective muscarinic M(3) antagonists that are based on the recently discovered triphenylpropioamide derivative, 1, and have a unique amino acid spacer group is described. The introduction of a hydroxyproline-proline group to the spacer site and the use of a propyl or cyclopropylmethyl group as the piperidine N-substituent led to the discovery of the novel M(3) selective antagonists [8c, 8g; K(i)700-fold, M(2)/M(3)>180-fold], which have a more rigid structure than 1.

PYRAZOLE DERIVATIVES

Disclosed are compounds of general formula (I), wherein R, R1, Rc, Rd, Re, Rf, X, Y, Z, A and B are as defined in the application.

PYRAZOLE DERIVATIVES

Disclosed are compounds of general formula (I), wherein R, R1, Rc, Rd, Re, Rf, X, Y, Z, A and B are as defined in the application.

ORTHO PYRROLIDINE, BENZYL-SUBSTITUTED HETEROCYCLE CCR1 ANTAGONISTS FOR AUTOIMMUNE DISEASES and INFLAMMATION

Compounds of the formula are disclosed. The compounds are CCR1 antagonists which are useful for the treatment and prevention of inflammatory and autoimmune diseases. Other embodiments are also disclosed.

Large nonlinear effect observed in the enantiomeric excess of proline in solution and that in the solid state

(Chemical Equation Presented) A clue to the origin of chirality? A solution of proline with high enantiomeric excess (85-99% ee) was obtained from solid proline of only 10% ee through novel dissolution and crystallization processes (see scheme). This observation may be an explanation for the origin of chirality on Earth.

Identification of a novel 4-aminomethylpiperidine class of M3 muscarinic receptor antagonists and structural insight into their M3 selectivity

Identification of a novel class of potent and highly selective M 3 muscarinic antagonists is described. First, the structure-activity relationship in the cationic amine core of our previously reported triphenylpropionamide class of M3 selective antagonists was explored by a small diamine library constructed in solid phase. This led to the identification of M3 antagonists with a novel piperidine pharmacophore and significantly improved subtype selectivity from a previously reported class. Successive modification on the terminal triphenylpropionamide part of the newly identified class gave 14a as a potent M3 selective antagonist that had > 100-fold selectivity versus the M1, M 2, M4, and M5 receptors (M3: K i = 0.30 nM, M1/M3 = 570-fold, M 2/M3 = 1600-fold, M4/M3 = 140-fold, M5/M3 = 12000-fold). The possible rationale for its extraordinarily higher subtype selectivity than reported M3 antagonists was hypothesized by sequence alignment of multiple muscarinic receptors and a computational docking of 14a into transmembrane domains of M3 receptors.

Enzyme-catalyzed enantiomeric resolution of N-Boc-proline as the key-step in an expeditious route towards RAMP

For the preparation of both enantiomers of N-carbamoyl-2-methoxymethylpyrrolidine, the precursors of Enders' chiral auxiliaries, SAMP and RAMP, enzyme-catalyzed kinetic resolution of racemic N-carbamoyl, N-Boc, N-Cbz proline esters and prolinols were examined. B. licheniformis protease (subtilisin) preferentially hydrolyzed the (R)-carbamoylproline ester with an enantiomeric ratio (E) of 10. To a hydrophobic N-Cbz proline ester, subtilisin showed lower selectivity (E=2.8), and in contrast, a purified protease (isozyme A) from the earthworm showed the preference of (S)-enantiomer (E=13.6). In a practical sense, C. antarctica lipase B (Chirazyme L-2) was effective for the hydrolysis of both N-Boc and N-Cbz derivatives with E >100. The e.e. of (R)-N-carbamoyl-2-methoxymethylpyrrolidine was raised to be >99.9% by recrystallization at the N-Boc-prolinol stage, which was derived from the (R)-N-Boc-proline methyl ester (98.7% e.e.) through a preparative-scale enzyme-catalyzed resolution (49% yield) of the racemic substrate.

Facile new method for preparation of optically active protected proline

Treatment of L-N-protected 2-amino-5-bromopentanoic acid ester, which was prepared from protected L-glutamic acid, with sodium hydride in tetrahydrofuran (THF) proceeded to give the corresponding protected L-proline in high yield. On the other hand, the reaction of 2-aminobutyric acid derivative with sodium hydride gave the 1-aminocyclopropane-1-carboxylic acid derivative.