BOC-11-AMINOUNDECANOIC ACID

BOC-11-AMINOUNDECANOIC ACID Property

Melting point:

67-68 °C

Boiling point:

441.9±18.0 °C(Predicted)

Density 

1.006±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

4.78±0.10(Predicted)

color 

White to Almost white

BRN 

1975656

InChI

InChI=1S/C16H31NO4/c1-16(2,3)21-15(20)17-13-11-9-7-5-4-6-8-10-12-14(18)19/h4-13H2,1-3H3,(H,17,20)(H,18,19)

InChIKey

HPTPZJBSQUULAV-UHFFFAOYSA-N

SMILES

C(O)(=O)CCCCCCCCCCNC(OC(C)(C)C)=O

CAS DataBase Reference

10436-25-6(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

2924.19.8000

HazardClass 

IRRITANT

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

BOC-11-AMINOUNDECANOIC ACID Chemical Properties,Usage,Production

Description

Boc-11-aminoundecanoic acid is an alkane chain with terminal carboxlic acid and Boc-protected amino groups. The compound can be used as a PROTAC linker in the synthesis of PROTACs. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond. The Boc group can be deprotected under mild acidic conditions to form the free amine.

Chemical Properties

White powder

Uses

Boc-11-aminoundecanoic acid is an Alkyl/ether-based?PROTAC linker?can be used in the synthesis of MS432 (HY-130602)[1].

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

General procedure for the synthesis of Boc-11-aminoundecanoic acid from 11-aminoundecanoic acid and di-tert-butyl dicarbonate: 160 g of 11-aminoundecanoic acid, 2 liters of dioxane, 1.3 liters of distilled water, 208 g of sodium carbonate, and 173 g of di-tert-butyl dicarbonate were added sequentially to a 4-liter three-necked flask in a unit equipped with a mechanical stirrer and reflux condenser. The reaction mixture was heated to boiling point and the reaction was continued with stirring for 16 hours to obtain a clarified solution. Upon completion of the reaction, the mixture was cooled to 20 °C and subsequently poured into 800 g of ice and the pH was adjusted to 3-4 with 4 N hydrochloric acid, at which point a white precipitate was produced. The precipitate was separated by filtration, washed with 300 cm3 of water and then dried under reduced pressure at 20 °C (20 mm Hg, 2.7 kPa) to give 232 g of N-(tert-butoxycarbonyl)-11-aminoundecanoic acid in 95% yield. The melting point of the product (68°C) is in agreement with that reported in the literature J. Org. Chem. 1997,1987.Chem., 41,1350 (1976).

IC 50

Alkyl/ether

References

[1] Wei J, et al.Discovery of a First-in-Class Mitogen-Activated Protein Kinase Kinase 1/2 Degrader.J Med Chem. 2019 Dec 12;62(23):10897-10911. DOI:10.1021/acs.jmedchem.9b01528