BOC-N-Methyl-L-alanine Chemical Properties

Melting point:

88-92 °C

Boiling point:

296.3±19.0 °C(Predicted)

Density 

1.111±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)

form 

Solid

pka

4.03±0.10(Predicted)

color 

White

optical activity

[α]20/D 30±1°, c = 1% in ethanol

BRN 

2366513

InChI

InChI=1S/C9H17NO4/c1-6(7(11)12)10(5)8(13)14-9(2,3)4/h6H,1-5H3,(H,11,12)/t6-/m0/s1

InChIKey

VLHQXRIIQSTJCQ-LURJTMIESA-N

SMILES

C(O)(=O)[C@H](C)N(C(OC(C)(C)C)=O)C

CAS DataBase Reference

16948-16-6(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

2924 19 00

HazardClass 

IRRITANT

MSDS

• Language:English Provider:SigmaAldrich

BOC-N-Methyl-L-alanine Usage And Synthesis

Chemical Properties

White powder

Uses

Boc-N-methyl-L-alanine can be used in peptide synthesis.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

General method: (S)-2-(tert-butoxycarbonylamino)-3-hydroxypropanoic acid (1 eq.) and iodomethane (10 eq.) were dissolved in anhydrous THF under nitrogen protection and cooled to 0 °C. Pure sodium hydride (10 eq.) was added in batches over 2.0 h. The reaction mixture was kept stirred at 0°C. Subsequently, the reaction mixture was continued to be stirred at room temperature for 24 hours. Upon completion of the reaction, the reaction mixture was diluted with ether (20 mL) and quenched with water (30 mL). The organic layer was separated and the aqueous layer was extracted with ether (2 x 15 mL). The combined organic layers were adjusted to pH 3 with aqueous citric acid and then extracted with EtOAc (3 x 20 mL). The combined EtOAc extracts were dried with anhydrous Na2SO4 and concentrated under reduced pressure to give BOC-N-methyl-L-alanine in 90% yield as a colorless oil.

References

[1] Tetrahedron, 2006, vol. 62, # 2-3, p. 264 - 284
[2] Chemistry - A European Journal, 2013, vol. 19, # 32, p. 10619 - 10624
[3] British Journal of Pharmacology, 2016, p. 2657 - 2668
[4] Medicinal Chemistry Research, 2016, vol. 25, # 6, p. 1148 - 1162
[5] Canadian Journal of Chemistry, 1977, vol. 55, p. 906 - 910

BOC-N-Methyl-L-alanine(16948-16-6)Related Product Information

• Phenprobamate
• N-Methyl-L-alanine
• L-Alanine
• Bensulfuron methyl
• D-Alanine
• Kresoxim-methyl
• N-(tert-Butoxycarbonyl)-L-alanine
• Methyl salicylate
• EC 2.6.1.2
• Boc-Aib-OH
• tert-Butyldimethylsilyl chloride
• TRIMETHYLPHOSPHINE OXIDE
• N-Boc-L-valine
• METSULFURON METHYL
• Methylparaben
• Fmoc-Lys(Boc)-OH
• Thiophanate-methyl
• BOC-L-Serine