FMOC-N-Methyl-L-alanine Chemical Properties

Melting point:

~150 °C

alpha 

-18.5 º (c=1,DMF)

Boiling point:

514.9±29.0 °C(Predicted)

Density 

1.262±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Soluble in water or 1% acetic acid

pka

3.92±0.10(Predicted)

form 

Solid

color 

White to Almost white

optical activity

[α]20/D 18.5±1°, c = 1% in DMF

Water Solubility 

Slightly soluble in water.

BRN 

4329998

Sequence

Fmoc-N-Me-Ala-OH

InChIKey

JOFHWKQIQLPZTC-LBPRGKRZSA-N

CAS DataBase Reference

84000-07-7(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

2924 29 70

HazardClass 

IRRITANT

MSDS

• Language:English Provider:SigmaAldrich

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

Chemical Properties

White to off white powder

Uses

It is a important organic intermediate. It can be used in agrochemical, pharmaceutical and dyestuff field. Also used in N-methyl amino acids for peptide synthesis.

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

The general procedure for the synthesis of Fmoc-N-methyl-L-alanine from the compound (CAS: 83999-95-5) was as follows: paraformaldehyde (4.0 g, 133 mmol) and p-toluenesulfonic acid (0.5 g, 13.3 mmol) were added to a suspension of Fmoc-L-alanine (6.2 g, 19.9 mmol) in toluene (400 mL). The mixture was refluxed for 30 min to remove azeotropic water. The solution was cooled, washed with 1 M aqueous NaHCO3 (2 x 100 mL) and dried with Na2SO4. Subsequently, the solution was concentrated in vacuum to give a white solid. The above oxazolidinone was dissolved in chloroform (75 mL) and trifluoroacetic acid (75 mL) and triethylsilane (7.2 mL, 44.8 mmol) were added. The reaction mixture was stirred at room temperature for 10 hours and then concentrated under vacuum. The resulting oily substance was dissolved in dichloromethane and the concentration was repeated three times. After standing, the oily substance crystallized. The crystals were redissolved in ether and concentrated. Finally, the collected white solid was washed with 5% ether/hexane and dried to give the product (6.1 g, 94% yield).

References

[1] Tetrahedron Letters, 2011, vol. 52, # 30, p. 3872 - 3875
[2] European Journal of Organic Chemistry, 2013, # 21, p. 4509 - 4513
[3] Journal of Organic Chemistry, 2005, vol. 70, # 17, p. 6918 - 6920
[4] Tetrahedron Letters, 2006, vol. 47, # 11, p. 1691 - 1694
[5] Tetrahedron Letters, 2014, vol. 55, # 44, p. 6109 - 6112

FMOC-N-Methyl-L-alanine(84000-07-7)Related Product Information

• N-Methyl-L-alanine
• FMOC-Ala-OH
• Methyl salicylate
• Fmoc-Lys(Boc)-OH
• Methyl acrylate
• Methanol
• Kresoxim-methyl
• DL-Alanine
• D-Alanine
• β-Alanine
• L-Fmoc-Aspartic acid alpha-tert-butyl ester
• 9-Fluorenylmethyl chloroformate
• EC 2.6.1.2
• FMOC-b-Ala-OH
• L-Alanine
• Phenprobamate
• Fmoc-Phe-OH
• Fmoc-Asp(OtBu)-OH