62937-47-7

Basic information

• Product Name: Z-D-PRO-NH2
• Synonyms: (R)-2-CARBAMOYL-1-CBZ-PYRROLIDINE;1-CBZ-D-PROLINAMIDE;Benzyloxycarbonyl-L-prolinamide, Carbobenzyloxy-L-prolinamide;(R)-2-Carbamoyl-1-N-Cbz-pyrrolidine;Cbz-D-prolinaMide;(R)-benzyl 2-carbamoylpyrrolidine-1-carboxylate;Cbz-D-Pro-NH2;(R)-Z-pyrrolidine-2-carboxylic acid amide
• CAS NO: 62937-47-7
• Molecular Formula: C₁₃H₁₆N₂O₃
• Molecular Weight: 248.28
• Product Categories: chiral;Chiral Reagent
• Mol File: 62937-47-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 90-95 °C
• Boiling Point: 465.6 °C at 760 mmHg
• Flash Point: 235.4 °C
• Appearance: /
• Density: 1.263 g/cm³
• Vapor Pressure: 7.61E-09mmHg at 25°C
• Refractive Index: 1.581
• Storage Temp.: Store at RT.
• PKA: 15.95±0.20(Predicted)
• CAS DataBase Reference: Z-D-PRO-NH2(CAS DataBase Reference)
• NIST Chemistry Reference: Z-D-PRO-NH2(62937-47-7)
• EPA Substance Registry System: Z-D-PRO-NH2(62937-47-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 62937-47-7(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C13H16N2O3/c14-12(16)11-7-4-8-15(11)13(17)18-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H2,14,16)/t11-/m1/s1

Upstream product

• 2812-47-7 pyrrolidine-2-carboxylic acid amide 
• 6404-31-5 Z-D-proline 
• 61350-62-7 N-benzyloxycarbonyl-D-proline acid chloride 
• 501-53-1 benzyl chloroformate 
• 344-25-2 D-Prolin 
• 15246-82-9 N-carbobenzoxy-(R)-proline-p-nitrophenol ester 

Downstream Products

• 62937-45-5 (R)-prolinamide 
• 839711-73-8 (2R)-2-(1H-tetrazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 702700-79-6 (R)-5-(pyrrolidin-2-yl)-1H-tetrazole 
• 57734-57-3 (-)-(R)-2-aminomethylpyrrolidine 
• 1140496-36-1 (R,E)-benzyl 2-(((dimethylamino)methylene)carbamoyl)pyrrolidine-1-carboxylate 
• 1140496-43-0 (R)-benzyl 2-(2-(4-chlorobenzyl)-5-methyl-2H-1,2,4-triazol-3-yl)pyrrolidine-1-carboxylate 
• 1137881-74-3 (R)-benzyl 2-(4-methylthiazol-2-yl)pyrrolidine-1-carboxylate 
• 1137881-73-2 (R)-benzyl 2-carbamothioylpyrrolidine-1-carboxylate 
• 1342299-30-2 N-((1R,2S)-1-hydroxy-3-phenyl-1-((R)-pyrrolidin-2-yl)propan-2-yl)-5-((R)-2-(4-methylthiazol-2-yl)pyrrolidine-1-carbonyl)chroman-7-carboxamide 
• 1342299-98-2 C₃₇H₄₆N₄O₆S 
• 1342299-93-7 (R)-tert-butyl 2-((1S,2S)-1-hydroxy-2-(6-((R)-2-(4-methylthiazol-2-yl)pyrrolidine-1-carbonyl)-2,3,4,5-tetrahydrobenzo[b]oxepine-8-carboxamido)-3-phenylpropyl)pyrrolidine-1-carboxylate 
• 620601-77-6 (+)-(R)-2-cyano-pyrrolidine-1-carboxylic acid benzyl ester 

Relevant articles and documents

Catalyst Repurposing Sequential Catalysis by Harnessing Regenerated Prolinamide Organocatalysts as Transfer Hydrogenation Ligands

A catalyst repurposing strategy based on a sequential aldol addition and transfer hydrogenation giving access to enantiomerically enriched α-hydroxy-γ-butyrolactones is described. The combination of a stereoselective, organocatalytic step, followed by an efficient catalytic aldehyde reduction induces an ensuing lactonization to provide enantioenriched butyrolactones from readily available starting materials. By capitalizing from the capacity of prolineamides to act as both an organocatalyst and a transfer hydrogenation ligand, catalyst repurposing allowed the development of an operationally simple, economic, and efficient sequential catalysis approach.

MACROCYCLIC MCL-1 INHIBITORS AND METHODS OF USE

The present disclosure provides for compounds of Formula (I) wherein A2, A3, A4, A6, A7, A8, A15, RA, R5, R9, R10A, R10B, R11, R12, R13, R14, R16, W, X, and Y have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions, including cancer. Also provided are pharmaceutical compositions comprising compounds of Formula (I).

Total Synthesis of the Marine Natural Product Hemiasterlin by Organocatalyzed α-Hydrazination

An efficient synthesis of the potently cytotoxic marine peptide hemiasterlin is presented. The tetramethyltryptophan moiety is assembled by tert-prenylation of indole, followed by the high-yielding organocatalyzed α-hydrazination of a sterically congested aldehyde with excellent enantioselectivity. 2-Bromo-N-ethylpyridinium tetrafluoroborate (BEP)-mediated peptide coupling completes the synthesis, being the first approach that does not employ chiral auxiliaries. A novel phenonium-type rearrangement of the indole system occurred when subjecting dihydroxylated 3-tert-prenylindole to Mitsunobu conditions.