69610-41-9

Basic information

• Product Name: N-BOC-L-Prolinal
• Synonyms: BOC-L-PROLINAL;N-BOC-L-PROLINAL;(S)-tert-Butyl 2-formylpyrrolidine-1-carboxylate;2-Formylpyrrolidine-1-carboxylic acid tert-butyl ester;(S)-N-Boc-pyrrolidine-2-carboxaldehyde, N-(tert-Butoxycarbonyl)-L-prolinal;(S)-N-BOC-Prolinal,97%;N-(Tert-butoxycarbonyl)-L-prol;(S)-1-Boc-2-forMylpyrrolidine
• CAS NO: 69610-41-9
• Molecular Formula: C₁₀H₁₇NO₃
• Molecular Weight: 199.25
• EINECS: 1592732-453-0
• Product Categories: Amino Aldehydes;Aldehydes;Amino Acid Derivatives;Building Blocks;C10-C12;Carbonyl Compounds;Chemical Biology;Chemical Synthesis;Organic Building Blocks;Peptide Chemistry;Heterocycles
• Mol File: 69610-41-9.mol
• Article Data: 178

Chemical Properties

• Boiling Point: 211 °C(lit.)
• Flash Point: 135 °F
• Appearance: clear light yellow viscous liquid
• Density: 1.063 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00483mmHg at 25°C
• Refractive Index: n20/D 1.462(lit.)
• Storage Temp.: Store at 0-5°C
• PKA: -3.03±0.40(Predicted)
• Water Solubility: Slightly soluble water. Soluble in chloroform.
• Sensitive: Air Sensitive
• CAS DataBase Reference: N-BOC-L-Prolinal(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-L-Prolinal(69610-41-9)
• EPA Substance Registry System: N-BOC-L-Prolinal(69610-41-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: 1989
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 69610-41-9(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 69610-41-9 differently. You can refer to the following data:
1. Key building block for norsecurinine-type alkaloids and isaindigotidione carboskeleton.1,2
2. Key building block for norsecurinine-type alkaloids and isaindigotidione carboskeleton.

InChI:InChI=1/C10H17NO3/c1-10(2,3)14-9(13)11-6-4-5-8(11)7-12/h7-8H,4-6H2,1-3H3/t8-/m1/s1

Upstream product

• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 201230-82-2 carbon monoxide 
• 73286-71-2 N-(tert-butoxycarbonyl)-2,3-dihydropyrrole 
• 79-37-8 oxalyl dichloride 
• 67-68-5 dimethyl sulfoxide 
• 459142-82-6 Boc-Pro-SEt 
• 135097-23-3 (2S)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 115186-37-3 tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 6216-63-3 N-Cbz-Prolinol 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 883565-15-9 C₁₅H₂₅NO₅ 

Downstream Products

• 123172-75-8 2-hydroxy-4-methyoxy<1-(tert-butoxycarbonylamino)-2-pyrrolidinyl>benzenemethanol 
• 123172-79-2 (S)-2-[(S)-Hydroxy-(2-hydroxy-4-methoxy-phenyl)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 123172-76-9 2-hydroxy-3-tert-butyl-α<1-(tertbutyloxycarbonylamino)-2-pyrrolidinyl>benzenemethanol 
• 130832-49-4 (S)-2-[(R)-(3-tert-Butyl-2-hydroxy-phenyl)-hydroxy-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 130832-50-7 (S)-2-[(R)-Hydroxy-(2-hydroxy-5-methoxy-phenyl)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 123172-77-0 (S)-2-[(S)-Hydroxy-(2-hydroxy-5-methoxy-phenyl)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 156574-94-6 (S)-2-(Benzyl-hydrazonomethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 123172-78-1 (S)-2-[(S)-Hydroxy-(2-hydroxy-phenyl)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 173441-05-9 tert-butyl (3R,4S,5S)-4-(N-benzyloxycarbonylamino)-3-methoxy-5-methylheptanoate 
• 173653-47-9 benzyl (2S,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate 
• 163768-51-2 benzyl (2R,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate 
• 130418-90-5 (S)-tert-butyl 2-ethynylpyrrolidine-1-carboxylate 
• 757956-31-3 C₁₇H₂₅N₃O₄S 
• 333363-48-7 N-Boc-Pro-ψ(NHCH2)-N-methyl-leucine benzyl ester 

Relevant articles and documents

Larger scale Stahl oxidation with instant Cu removal in convenient synthesis of chiral bidentate N–heterocyclic carbene precursor

Commercially available N-Boc protected L-proline can be efficiently converted into a chiral, bidentate, aminoalkyl N-heterocyclic carbene ligand precursor in high yield (50% total after 4 steps) without column chromatography purification at any moment. The developed synthetic path includes: (1) redox step leading to an aldehyde, (2) imine condensation and in situ reduction to 1,2-diamine; (3) heterocyclization; (3) removal of the protecting group. Instant separation of Cu traces after the key Stahl oxidation at gram-scale was facilitated by the use of bis(isocyanide) scavenger, SnatchCat, forming insoluble, easy to remove RNC:→[Cu] complexes that allowed usto obtain crude intermediate suitably pure for next steps without tedious purification.

NOVEL CONNECTED BODY AND USE THEREOF IN SPECIFIC CONJUGATION BETWEEN BIOMOLECULE AND DRUG

PROBLEM TO BE SOLVED: To provide: a method for producing a connected body; a method for using the connected body in the production of a uniform conjugate; and a method for applying the conjugate in the treatment of cancer, infectious diseases, and autoimmune diseases. SOLUTION: A novel connected body is provided that includes a 2,3-di-substituted succinic acid group or a 2-mono-substituted or 2,3-di-substituted fumaric acid or maleic acid (trans (E)- or cis (Z)-butenedioic acid) group for conjugating 2 or more compounds/cytotoxic agents per connected body with a cell-binding molecule by specifically bridge-linking to a pair of thiol on the cell-binding molecule. The connected body is exemplified by the following general formula. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

X-ray Structure-Guided Discovery of a Potent, Orally Bioavailable, Dual Human Indoleamine/Tryptophan 2,3-Dioxygenase (hIDO/hTDO) Inhibitor That Shows Activity in a Mouse Model of Parkinson’s Disease

Human indoleamine 2,3-dioxygenase 1 (hIDO1) and tryptophan 2,3-dioxygenase (hTDO) have been closely linked to the pathogenesis of Parkinson’s disease (PD); nevertheless, development of dual hIDO1 and hTDO inhibitors to evaluate their potential efficacy against PD is still lacking. Here, we report biochemical, biophysical, and computational analyses revealing that 1H-indazole-4-amines inhibit both hIDO1 and hTDO by a mechanism involving direct coordination with the heme ferrous and ferric states. Crystal structure-guided optimization led to23, which manifested IC50values of 0.64 and 0.04 μM to hIDO1 and hTDO, respectively, and had good pharmacokinetic properties and brain penetration in mice.23showed efficacy against the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse motor coordination deficits, comparable to Madopar, an anti-PD medicine. Further studies revealed that different from Madopar,23likely has specific anti-PD mechanisms involving lowering IDO1 expression, alleviating dopaminergic neurodegeneration, reducing inflammatory cytokines and quinolinic acid in mouse brain, and increasing kynurenic acid in mouse blood.