Boc-L-beta-homoglutamic acid 6-benzyl ester Chemical Properties

Boiling point:

530.0±45.0 °C(Predicted)

Density 

1.178±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

Powder

pka

4.35±0.10(Predicted)

CAS DataBase Reference

218943-30-7

Safety Information

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29242990

MSDS

• Language:English Provider:SigmaAldrich

Boc-L-beta-homoglutamic acid 6-benzyl ester Usage And Synthesis

Chemical Properties

White powder

Uses

Starting materials for peptide synthesis, peptidomimetic and medicinal chemistry, protected amino acids, coupling reagents, linkers and resins, natural and unusual amino acids and building blocks used in peptide synthesis, peptidomimetic and medicinal chemistry. Reagents for PEGylation, Life science Research and biocatalysis.

Uses

Boc-l-beta-homoglutamic acid 6-benzyl ester

Synthesis

The general procedure for the synthesis of (S)-6-(benzyloxy)-3-((tert-butoxycarbonyl)amino)-6-oxohexanoic acid from 6-benzyl 3-(tert-butoxycarbonyl)amino)adipate (6) was as follows: diazoxide (5) (3.00 g, 8.30 mmol) was dissolved in a 5:1 solvent mix of THF/H2O (60 ml), cooled in an ice bath, and aluminum foil was used to wrap the flask to avoid light. Subsequently, silver trifluoroacetate (0.37 g, 1.66 mmol) was added and NMM (2.28 ml, 20.75 mmol) was added dropwise. The reaction mixture was reacted under stirring for 4.5 hours and gradually warmed up to room temperature. After completion of the reaction, THF was removed by evaporation, 1N KHSO4 aqueous solution (40 ml) was added and the precipitate was removed by filtration. The aqueous phase was extracted with ethyl acetate and the organic phase was washed twice with 1N KHSO4 aqueous solution, dried over MgSO4 and then evaporated in vacuum to remove the solvent. The yellow crude product obtained was ground with ether to give the target compound as a white solid (2.17 g, 74% yield).1H NMR (CDCl3, 300 MHz) δ: 7.42-7.31 (m, 5H), 5.13 (s, 2H), 4.00 (m, 1H), 4.03-3.90 (m, 1H), 2.70-2.56 (m, 2H) , 2.54-2.40 (m, 2H), 1.98-1.85 (m, 2H), 1.45 (s, 9H).

References

[1] Patent: WO2017/37142, 2017, A1. Location in patent: Paragraph 00318; 00319
[2] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 20, p. 3331 - 3340
[3] Organic Letters, 2000, vol. 2, # 13, p. 1943 - 1946
[4] RSC Advances, 2014, vol. 4, # 70, p. 37419 - 37422

Boc-L-beta-homoglutamic acid 6-benzyl ester(218943-30-7)Related Product Information

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