Boc-6-AMinocaproic acid Chemical Properties

Melting point:

35-40 °C

Boiling point:

166°C/0.3mmHg(lit.)

Density 

1.065±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Chloroform, Ethyl Acetate

pka

4.76±0.10(Predicted)

form 

Powder

color 

White

Water Solubility 

Soluble in chloroform and ethyl acetate. Slightly soluble in water.

BRN 

2049561

InChI

InChI=1S/C11H21NO4/c1-11(2,3)16-10(15)12-8-6-4-5-7-9(13)14/h4-8H2,1-3H3,(H,12,15)(H,13,14)

InChIKey

RUFDYIJGNPVTAY-UHFFFAOYSA-N

SMILES

C(O)(=O)CCCCCNC(OC(C)(C)C)=O

CAS DataBase Reference

6404-29-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-26

WGK Germany 

3

F 

21

HazardClass 

IRRITANT

HS Code 

29241990

MSDS

• Language:English Provider:SigmaAldrich

Boc-6-AMinocaproic acid Usage And Synthesis

Description

Boc-6-aminohexanoic 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 and other conjugation applications. 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

Colorless crystal

Uses

6-(Boc-amino)hexanoic acid is used in the preparation of esters of 6-aminohexanoic acid as antibacterial agents. EACA is reported to inhibit chymotrypsin, Factor VIIa, lysine carboxy peptidase, plasmin, and plasminogen activator.

Uses

Protected ε-Aminocaproic Acid (A603015), Boc-6-AMinocaproic acid can be used in the preparatiom of esters of 6-aminohexanoic acid.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

General procedure for the synthesis of tert-butoxycarbonyl 6-aminohexanoic acid from 6-aminohexanoic acid (20 g, 153 mmol) and di-tert-butyl dicarbonate (3.67 g, 16.8 mmol): 6-aminohexanoic acid was dissolved in dichloromethane (30 mL) followed by addition of di-tert-butyl dicarbonate. The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, the reaction mixture was filtered and the solvent was removed by distillation under reduced pressure. The crude product was dried under high vacuum to give 4.08 g (115% yield) of the target compound. The product was characterized by 400 MHz 1H NMR (DMSO-d6): δ 2.85 (q, J=13.2,6.8 Hz, 2H), 2.15 (t, J=1.2 Hz, 2H), 1.47-1.43 (m, 4H), 1.34 (s, 9H), 1.22-1.18 (m, 2H). the LCMS analysis showed m/z=232 [M +H]+.

IC 50

Alkyl/ether

References

[1] Organic and Biomolecular Chemistry, 2005, vol. 3, # 13, p. 2450 - 2457
[2] Patent: WO2009/26446, 2009, A2. Location in patent: Page/Page column 30
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 14, p. 4358 - 4369
[4] Chemical Communications, 2006, # 36, p. 3783 - 3785
[5] Synthesis, 1988, # 3, p. 259 - 261

Boc-6-AMinocaproic acid(6404-29-1)Related Product Information

• N-ALPHA-T-BUTYLOXYCARBONYL-L-NORLEUCINE DICYCLOHEXYLAMINE, (S)-N-ALPHA-BOC-2-AMINOHEXANOIC ACID,(S)-N-ALPHA-BOC-2-AMINOHEXANOIC ACID DICYCLOHEXYLAMINE
• BOC-SAR-OH
• Boc-N-beta-Trityl-L-asparagine
• N-tert-Butoxycarbonyl-L-glutamic acid gamma-tert-butyl ester
• Boc-L-aspartic acid 4-tert-butyl ester
• Succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate
• Boc-L-glutamic acid 5-cyclohexyl ester
• Boc-D-aspartic acid 4-benzyl ester
• BOC-GLU(OFM)-OH
• BOC-PHE-SER-ARG-AMC ACETATE SALT
• BOC-ORN-OH
• BOC-D-Alanine
• (BOC-AMINOOXY)ACETIC ACID
• N-Boc-L-valine
• Boc-beta-alanine
• Boc-Arg(Tos)-OH
• Boc-L-aspartic acid 1-benzyl ester
• BOC-4-IODO-L-PHENYLALANINE