176982-58-4

Basic information

• Product Name: (3-BENZYLAMINO-1-METHYL-PROPYL)-CARBAMIC ACID TERT-BUTYL ESTER
• Synonyms: tert-Butyl (4-(benzylaMino)butan-2-yl)carbaMate;(3-BENZYLAMINO-1-METHYL-PROPYL)-CARBAMIC ACID TERT-BUTYL ESTER
• CAS NO: 176982-58-4
• Molecular Formula: C₁₆H₂₆N₂O₂
• Molecular Weight: 278.39
• Mol File: 176982-58-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 400.9°Cat760mmHg
• Flash Point: 196.2°C
• Appearance: /
• Density: 1.009g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.505
• CAS DataBase Reference: (3-BENZYLAMINO-1-METHYL-PROPYL)-CARBAMIC ACID TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (3-BENZYLAMINO-1-METHYL-PROPYL)-CARBAMIC ACID TERT-BUTYL ESTER(176982-58-4)
• EPA Substance Registry System: (3-BENZYLAMINO-1-METHYL-PROPYL)-CARBAMIC ACID TERT-BUTYL ESTER(176982-58-4)

Safety Data

• Hazardous Substances Data: 176982-58-4(Hazardous Substances Data)

Usage

General Description

(3-Benzylamino-1-methyl-propyl)-carbamic acid tert-butyl ester is a chemical compound that belongs to the class of carbamic acid esters. It is a white to off-white solid that is soluble in organic solvents. The compound is commonly used in organic synthesis as a reagent and intermediate for the preparation of various pharmaceuticals and agrochemicals. Its chemical structure consists of a tert-butyl ester group, a carbamate group, and a benzylamino-methyl-propyl moiety. It is important to handle this chemical with care and follow proper safety protocols when working with it.

InChI:InChI=1/C16H26N2O2/c1-13(18-15(19)20-16(2,3)4)10-11-17-12-14-8-6-5-7-9-14/h5-9,13,17H,10-12H2,1-4H3,(H,18,19)/t13-/m0/s1

Upstream product

• 176982-57-3 (3-amino-1(S)-methylpropyl)carbamic acid, 1,1-dimethylethyl ester 
• 172695-22-6 (2-cyano-1(S)-methylethyl)carbamic acid, 1,1-dimethylethyl ester 
• 126301-16-4 (2S)-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate 
• 79069-13-9 (S)-2-t-butoxycarbonylaminopropan-1-ol 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 170367-79-0 [4-[[3-[[(1,1-dimethylethoxy)carbonyl]amino]butyl](phenylmethyl)amino]butyl]carbamic acid, 11-[[(1,1-dimethylethoxy)carbonyl]amino]-15,15-dimethyl-2,13-dioxo-14-oxa-3,4,12-triaza-11-hexadecen-1-yl ester (S) 
• 252353-89-2 [21-[[(1,1-dimethylethoxy)carbonyl]amino]-1,25,25-trimethyl-10,12,23-trioxo-4-(phenylmethyl)-24-oxa-4,9,13,20,22-pentaaza-21-hexacosen-1-yl]carbamic acid, 1,1-dimethylethyl ester (S) 
• 170367-77-8 2,2,6-trimethyl-4,15-dioxo-9-(phenylmethyl)-3,16-dioxa-5,9,14-triazaoxadecan-18-oic acid (S) 
• 252353-70-1 [3-[[4-(2,4-dioxo-3-oxazolidinyl)butyl](phynylmethyl)amino]-1-methylpropyl]carbamic acid, 1,1-dimethylethyl ester (S) 
• 170367-73-4 3-[(4-aminobutyl)(phenylmethyl)amino-1(S)-methylpropyl]carbamic acid, 1,1-dimethylethyl ester 
• 176982-59-5 3-[(3-cyanopropyl)(phenylmethyl)amino-1(S)-methylpropyl]carbamic acid, 1,1-dimethylethyl ester 

Relevant articles and documents

Structure - Immunosuppressive activity relationships of new analogues of 15-deoxyspergualin. 2. Structural modifications of the spermidine moiety

A series of new analogues of 15-deoxyspergualin (DSG), an immunosuppressive agent commercialized in Japan, was synthesized and tested in a graft-versus-host disease (GVHD) model in mice. Various substitutions of the spermidine 'D' region were made in order to determine its optimum structure in terms of in vivo immunosuppressive activity. Various positions of methylation were first investigated leading to the discovery of the monomethylated malonic derivative 56h in which the pro-R hydrogen of the methylene α to the primary amine of the spermidine moiety has been replaced by a methyl group. Synthesis of the similarly methylated analogue of the previously reported glycolic derivative LF 08-0299 afforded 60c which demonstrated a powerful activity at a dose as low as 0.3 mg/kg in the GVHD model and was much more potent than DSG in the demanding heart allotransplantation model in rats. The improvement of in vivo activity was supposed to be related to an increase of the metabolic stability of the methylated analogues compared to the parent molecules. Due to its very low active dose, compatible with a subcutaneous administration in humans, and its favorable pharmacological and toxicological profile, 60e was selected as a candidate for clinical evaluation.