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FMOC-N-Methyl-L-alanine

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CAS:84000-07-7
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  • Fmoc-L-N-Me-Ala-OH
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  • 2021-08-12
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FMOC-N-Methyl-L-alanine Basic information
Product Name:FMOC-N-Methyl-L-alanine
Synonyms:(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}(methyl)amino)propanoic acid;Fmoc-N-Me-DL-Alanine;Fmoc-N-methyl-L-alanine≥ 99% (HPLC);(9H-Fluoren-9-yl)MethOxy]Carbonyl N-Me-Ala-OH;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-alanine;(S)-2-((((9H-Fluoren-9-yl)Methoxy)carbonyl)(Methyl)aMino)propanoic acid;N-FMoc-N-Methyl-L-alanine, 95%;Fmoc-N-Me-L-Alanine
CAS:84000-07-7
MF:C19H19NO4
MW:325.36
EINECS:1533716-785-6
Product Categories:Amino Acids;Alanine [Ala, A];N-Methyl Amino Acids;Fmoc-Amino acid series
Mol File:84000-07-7.mol
FMOC-N-Methyl-L-alanine Structure
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
pka3.92±0.10(Predicted)
form Solid
color White to Almost white
Optical Rotation[α]20/D 18.5±1°, c = 1% in DMF
Water Solubility Slightly soluble in water.
BRN 4329998
SequenceFmoc-N-Me-Ala-OH
Major Applicationpeptide synthesis
InChI1S/C19H19NO4/c1-12(18(21)22)20(2)19(23)24-11-17-15-9-5-3-7-13(15)14-8-4-6-10-16(14)17/h3-10,12,17H,11H2,1-2H3,(H,21,22)/t12-/m0/s1
InChIKeyJOFHWKQIQLPZTC-LBPRGKRZSA-N
SMILESC[C@H](N(C)C(=O)OCC1c2ccccc2-c3ccccc13)C(O)=O
CAS DataBase Reference84000-07-7(CAS DataBase Reference)
Safety Information
Safety Statements 22-24/25
WGK Germany 3
HS Code 2924 29 70
HazardClass IRRITANT
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
SigmaAldrich English
FMOC-N-Methyl-L-alanine Usage And Synthesis
Chemical PropertiesWhite to off white powder
UsesIt 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 suitabilityreaction type: Fmoc solid-phase peptide synthesis
Synthesis
3-Oxazolidinecarboxylic acid, 4-methyl-5-oxo-, 9H-fluoren-9-ylmethyl ester, (4S)-

83999-95-5

FMOC-N-Methyl-L-alanine

84000-07-7

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 Preparation Products And Raw materials
Raw materials3-Oxazolidinecarboxylic acid, 4-methyl-5-oxo-, 9H-fluoren-9-ylmethyl ester, (4S)--->Trifluoroacetic acid-->Chloroform-->Triethylsilane
Tag: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