5545-52-8

Basic information

• Product Name: N-Cbz-L-Aspartic acid 4-tert-butyl ester
• Synonyms: CBZ-L-ASPARTIC ACID 4-TERT-BUTYL ESTER;N-CBZ-L-ASPARTIC ACID 4-TERT-BUTYL ESTER;N-BENZYLOXYCARBONYL-L-ASPARTIC ACID 4-TERT-BUTYL ESTER;Z-ASPARTIC ACID(OTBU)-OH;Z-ASP(OTBU)-OH;Z-L-ASPARTIC ACID 4-TERT-BUTYL ESTER;Z-L-ASP(OTBU)-OH;4-tert-butyl hydrogen N-[(phenylmethoxy)carbonyl]-L-aspartate
• CAS NO: 5545-52-8
• Molecular Formula: C₁₆H₂₁NO₆
• Molecular Weight: 323.34
• EINECS: 226-912-0
• Product Categories: AMINOACIDS DERIVATIVES;Aspartic acid [Asp, D];Z-Amino Acids and Derivatives;Z-Amino acid series
• Mol File: 5545-52-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 513.1 °C at 760 mmHg
• Flash Point: 264.1 °C
• Appearance: White powder
• Density: 1.219 g/cm³
• Vapor Pressure: 2.36E-11mmHg at 25°C
• Refractive Index: 1.526
• Storage Temp.: −20°C
• Solubility: Soluble in DMSO, and methanol.
• PKA: 3.67±0.23(Predicted)
• BRN: 2569846
• CAS DataBase Reference: N-Cbz-L-Aspartic acid 4-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Cbz-L-Aspartic acid 4-tert-butyl ester(5545-52-8)
• EPA Substance Registry System: N-Cbz-L-Aspartic acid 4-tert-butyl ester(5545-52-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 5545-52-8(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

Uses

It is a pharmaceutical intermediate.

InChI:InChI=1/C16H21NO6/c1-16(2,3)23-13(18)9-12(14(19)20)17-15(21)22-10-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,17,21)(H,19,20)/t12-/m0/s1

Upstream product

• 762-75-4 tert-butyl formate 
• 1152-61-0 N-Cbz-L-Asp 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 1634-04-4 tert-butyl methyl ether 
• 540-88-5 acetic acid tert-butyl ester 
• 585-07-9 tert-Butyl methacrylate 
• 774-65-2 benzoic acid tert-butyl ester 
• 20487-40-5 tert-butyl propionate 
• 4668-43-3 (S)-3-(benzyloxycarbonylamino)-4-ethoxy-4-oxobutanoic acid 
• 4515-23-5 N-benzyloxycarbonyl-L-aspartic acid anhydride 
• 4668-44-4 N-benzyloxycarbonyl-L-aspartic acid α-p-nitrobenzyl ester 
• 2131-29-5 (S)-1-benzyl-4-tert-butyl 2-aminosuccinate 
• 88966-25-0 N-benzyloxycarbonyl-L-aspartic anhydride 
• 4668-42-2 (S)-2-benzyloxycarbonylamino-succinic acid 1-methyl ester 

Downstream Products

• 157886-13-0 Z-Asp(Ot-Bu)-OTse 
• 25529-40-2 Z-L-Asp(OtBu)-OPFP 
• 156916-71-1 t-butyl N^α-benzyloxycarbonyl-L-glutaminyl-L-alanylglycyl-L-(β-t-butoxy)aspartyl-L-valinate 
• 156916-72-2 t-butyl N^α-benzyloxycarbonyl-L-(ε-butoxycarbonyl)lysyl-L-glutaminyl-L-alanylglycyl-L-(β-t-butoxy)aspartyl-L-valinate 
• 156916-73-3 t-butyl N^α-benzyloxycarbonyl-L-alanyl-L-(butoxycarbonyl)lysyl-L-glutaminyl-L-alanylglycyl-L-(β-t-butoxy)aspartyl-L-valinate 
• 156916-70-0 t-butyl N^α-benzyloxycarbonyl-L-alanylglycyl-L-(β-t-butoxy)aspartyl-L-valinate 
• 157886-17-4 Z-Glu(Ot-Bu)-Asp(Ot-Bu)-OPet 
• 157886-18-5 Z-Glu(Ot-Bu)-Asp(Ot-Bu)-OTce 
• 126027-29-0 Boc-Tyr-D-Ala-Asp(OBu^t)-Gly-Tyr-Pro-Ser-NH₂ 
• 126027-27-8 Boc-Tyr-D-Ala-Asp(OBu^t)-Gly-OH 
• 126027-23-4 Z-D-Ala-Asp(OBu^t)-Gly-OH 
• 153088-77-8 2,6-Dichloro-benzoic acid (S)-3-benzyloxycarbonylamino-4-tert-butoxycarbonyl-2-oxo-butyl ester 
• 153088-73-4 carbobenzoxy-L-aspart-1-yl-[(2,6-dichlorobenzoyl)oxy]-methane 
• 183498-67-1 (S)-3-Benzyloxycarbonylamino-N-{(R)-2-[(R)-2-((S)-2-benzyloxycarbonylamino-3-carboxy-propionylamino)-2-carboxy-ethyldisulfanyl]-1-carboxy-ethyl}-succinamic acid 

Relevant articles and documents

A versatile and selective chemo-enzymatic synthesis of β-protected aspartic and γ-protected glutamic acid derivatives

Two versatile, high yielding, and efficient chemo-enzymatic methods for the synthesis of β-protected Asp and γ-protected Glu derivatives using Alcalase are described. The first method is based on the α-selective enzymatic hydrolysis of symmetrical aspartyl and glutamyl diesters. The second method involving mixed diesters comprises a three-step protocol using (i) α-selective enzymatic methyl-esterification, (ii) chemical β-esterification, and finally (iii) α-selective enzymatic methyl ester hydrolysis. The yields of the purified β- and γ-esters range from 77% to 91%.

Facile synthesis of tert-butyl ester of N-protected amino acids with tert-butyl bromide

A facile synthesis of a wide variety of N-benzyloxycarbonyl-amino acid-tert-butyl ester derivatives under mild conditions is described. N-protected amino acids were esterified with tert-butyl bromide in dimethylacetamide as solvent, in the presence of benzyltriethylammonium chloride (BTEAC)and a large excess of potassium carbonate. Many amino Z-acid-Tert-butyl esters that might be difficult to prepare by other methods have been synthesized in high yields by this procedure. The reaction is simple, unexpansive, easily scaled up, and proceeds without observable racemization.

MONO-ESTERIFICATION OF N-PROTECTED DI-ACIDS ASPARTIC AND GLUTAMIC BY CHLOROFORMATE ACTIVATION

Mono-esters of N-protected di-acids aspartic and glutamic are prepared by a one-pot activation with alkyl chloroformates or isopropenyl chloroformate and an additionnal alcohol.This process involves the intermediate internal anhydride formation.