BOC-11-AMINOUNDECANOIC ACID Chemical Properties

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

2924.19.8000

HazardClass 

IRRITANT

MSDS

• Language:English Provider:SigmaAldrich

BOC-11-AMINOUNDECANOIC ACID Usage And Synthesis

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

BOC-11-AMINOUNDECANOIC ACID(10436-25-6)Related Product Information

• Undecanedioic acid
• 11-Aminoundecanoic acid
• 2-(1-(TERT-BUTOXYCARBONYL)PIPERIDIN-3-YL)CYCLOHEXANECARBOXYLIC ACID
• BOC-11-AMINOUNDECANOIC ACID