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BOC-L-Methionine

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CAS:2488-15-5
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  • 2025-09-25
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  • BOC-L-Methionine
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  • 2019-07-06
  • CAS:2488-15-5
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  • Purity: 99%
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BOC-L-Methionine Basic information
Product Name:BOC-L-Methionine
Synonyms:L-Methionine, N-[(1,1-dimethylethoxy)carbonyl]-;N-(tert-Butoxycarbonyl)-L-methionine ,98%;(S)-2-[(tert-Butyloxycarbonyl)amino]-4-(methylthio)butyric acid;Boc-L-methionine ,98%;Boc-Met-O;N-Boc-L-methionine Boc-Met-OH;(S)-2-((tert-butoxycarbonyl)aMino)-4-(Methylthio)butanoic acid;2-[(2-Methylpropan-2-yl)oxycarbonylamino]-4-methylsulfanylbutanoic acid
CAS:2488-15-5
MF:C10H19NO4S
MW:249.33
EINECS:219-639-3
Product Categories:Biochemistry;Boc-Amino Acids;Boc-Amino acid series;Methionine [Met, M];Boc-Amino Acids and Derivative;Amino Acid Derivatives;Amino Acids;Amino Acids (N-Protected)
Mol File:2488-15-5.mol
BOC-L-Methionine Structure
BOC-L-Methionine Chemical Properties
Melting point 47-50 °C(lit.)
alpha -23 º (c=1.3, methanol)
Boiling point 415.5±40.0 °C(Predicted)
density 1.160±0.06 g/cm3(Predicted)
refractive index -22 ° (C=1.3, AcOH)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility almost transparency in Methanol
pka3.83±0.10(Predicted)
form Powder
color White to off-white
Optical Rotation[α]20/D 22°, c = 1 in methanol
BRN 1727869
Major Applicationpeptide synthesis
InChI1S/C10H19NO4S/c1-10(2,3)15-9(14)11-7(8(12)13)5-6-16-4/h7H,5-6H2,1-4H3,(H,11,14)(H,12,13)/t7-/m0/s1
InChIKeyIMUSLIHRIYOHEV-ZETCQYMHSA-N
SMILESCSCC[C@H](NC(=O)OC(C)(C)C)C(O)=O
CAS DataBase Reference2488-15-5(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-36/37/38
Safety Statements 24/25-36-26
WGK Germany 3
9-23
HS Code 2930 90 98
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
Boc-D-Met-OH English
SigmaAldrich English
ACROS English
ALFA English
BOC-L-Methionine Usage And Synthesis
Chemical Propertieswhite to off-white microcrystalline powder
UsesN-Boc-L-methionine is an N-Boc-protected form of L-Methionine (M260440). L-Methionine is an essential amino acid that is obtained from our diet. L-Methionine can be found in grain legumes (such as lentils), and poultry. L-Methionine’s main function is to act as the primary “Start” sequence on mRNA so that the ribosomes can start translating the mRNA into proteins.
reaction suitabilityreaction type: Boc solid-phase peptide synthesis
Synthesis
L-Methionine

63-68-3

Di-tert-butyl dicarbonate

24424-99-5

BOC-L-Methionine

2488-15-5

Example 1 [0041] 7.2 g of L-methionine was dissolved in a solvent mixture of 50 mL of water and 50 mL of acetonitrile. To this solution was added 2 g of sodium hydroxide (0.05 mol). The reaction mixture was cooled to 0 °C, followed by the slow addition of 10.9 g of di-tert-butyl dicarbonate (0.05 mol). After addition, the reaction system was gradually warmed to room temperature (24-25 °C) and the reaction was continuously stirred for 12 hours. After completion of the reaction, the acetonitrile was removed by rotary evaporation. To the residual aqueous phase, potassium carbonate was added and the pH was adjusted to 12. The aqueous phase was extracted twice with 50 mL of dichloromethane and the organic phase was discarded. To the aqueous phase, 1 N hydrochloric acid was added dropwise and the pH was adjusted to 6. The aqueous phase was again extracted twice with 50 mL of dichloromethane, the organic phases were combined, washed with 50 mL of saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to give viscous Boc-L-methionine (11.4 g) in 95% yield. The product was characterized by 1H NMR (500 MHz, CDCl3): δ 11.62 (br, 1H), 6.91 (br, 1H), 4.40 (m, 1H), 2.52 (t, J = 4.8 Hz, 2H), 2.05 (s, 3H), 1.92-2.15 (m, 2H), 1.42 (s, 9H). Mass spectrometry (MS) showed a molecular ion peak (M + 1) of 250.

References[1] Antimicrobial Agents and Chemotherapy, 2017, vol. 61, # 3,
[2] Tetrahedron Letters, 1994, vol. 35, # 14, p. 2121 - 2124
[3] Patent: EP2647624, 2013, A1. Location in patent: Paragraph 0040; 0041
[4] Organic Syntheses, 1985, vol. 63, p. 160 - 160
[5] Tetrahedron Letters, 2018, p. 4267 - 4271
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