BOC-L-3-BENZOTHIENYLALANINE Chemical Properties

Boiling point:

514.1±45.0 °C(Predicted)

Density 

1.274±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

pka

3.85±0.10(Predicted)

Appearance

White to off-white Solid

BRN 

7081201

CAS DataBase Reference

154902-51-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

WGK Germany 

3

F 

10-23

HazardClass 

IRRITANT

HS Code 

2934999090

MSDS

• Language:English Provider:SigmaAldrich

BOC-L-3-BENZOTHIENYLALANINE Usage And Synthesis

Uses

peptide synthesis

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

General procedure for the synthesis of (S)-3-(benzo[b]thiophen-3-yl)-2-((tert-butoxycarbonyl)amino)propionic acid from di-tert-butyl dicarbonate and (S)-2-amino-3-(benz[b]thiophen-3-yl)propionic acid: to a THF:H2O (1.0 g, 4.52 mmol) solution containing K2CO3 (0.75 g, 5.33 mmol) and (S)-2-amino-3-(benzo[b]thieno -3-yl)propionic acid (1.0 g, 4.52 mmol) to a solution of THF:H2O (1:1, v/v) was slowly added di-tert-butyl dicarbonate (1.09 g, 5 mmol). Subsequently, the reaction mixture was gradually warmed to room temperature and stirred continuously overnight. Upon completion of the reaction, the mixture was concentrated to remove most of the solvent and then the residue was dissolved in a mixture of EtOAc and H2O. The pH of the aqueous phase was adjusted to 1-2 with 6N HCl, followed by three extractions with EtOAc. The organic layers were combined, dried with anhydrous Na2SO4, filtered and concentrated to give 1.22 g of the target product as a white foamy solid in 84% yield.

References

[1] Journal of Medicinal Chemistry, 1994, vol. 37, # 13, p. 2090 - 2099
[2] Patent: WO2005/85227, 2005, A1. Location in patent: Page/Page column 47; 117

BOC-L-3-BENZOTHIENYLALANINE(154902-51-9)Related Product Information

• BOC-L-2-AMINOMETHYLPHE(FMOC)
• Thianaphthene
• BOC-D-3-BENZOTHIENYLALANINE
• L-3-THIENYLALANINE
• BOC-L-3-BENZOTHIENYLALANINE
• 3-THIEN-3-YLPROPANOIC ACID
• 3-(3-benzo(b)thienyl)alanine
• BOC-(S)-ALPHA-(3-BENZOTHIOPHENYLMETHYL)-PROLINE
• BOC-L-3-THIENYLALANINE DCHA SALT
• BOC-3-(3-BENZOTHIENYL)-DL-ALANINE
• 3-THIOPHENEPROPIONIC ACID
• L-3-BENZOTHIENYLALANINE
• (2-THIOPHEN-3-YL-ETHYL)-CARBAMIC ACID TERT-BUTYL ESTER
• BOC-DL-3-THIENYLALANINE
• 3-(Benzo[b]thiophen-3-yl)propanoicacid