| Identification | More | [Name]
BOC-L-Methionine | [CAS]
2488-15-5 | [Synonyms]
BOC-L-MET
BOC-L-METHIONINE
BOC-L-METHIONINE-OH
BOC-L-MET-OH
BOC-MET
BOC-METHIONINE
BOC-MET-OH
N-[(1,1-DIMETHYLETHOXY)CARBONYL]-L-METHIONINE
N-ALPHA-T-BOC-L-METHIONINE
N-ALPHA-T-BUTOXYCARBONYL-L-METHIONINE
N-ALPHA-TERT-BUTYLOXYCARBONYL-L-METHIONINE
N-BOC-L-METHIONINE
N-T-BOC-L-METHIONINE
N-(TERT-BUTOXYCARBONYL)-L-METHIONINE
TBOC-L-METHIONINE
T-BUTYLOXYCARBONYL-L-METHIONINE
tert-butoxycarbonyl-L-methionine
N-T-BOC-L-METHIONINE FREE ACIDCRYSTALLIN E
N-(TERT-BUTOXYCARBONYL)-L-METHIONINE, 99 %
BOC-L-Methionine, 99+% | [EINECS(EC#)]
219-639-3 | [Molecular Formula]
C10H19NO4S | [MDL Number]
MFCD00065586 | [Molecular Weight]
249.33 | [MOL File]
2488-15-5.mol |
| Chemical Properties | Back Directory | [Appearance]
white to off-white microcrystalline powder | [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. ]
2-8°C
| [solubility ]
almost transparency in Methanol | [form ]
Powder | [pka]
3.83±0.10(Predicted) | [color ]
White to off-white | [Optical Rotation]
[α]20/D 22°, c = 1 in methanol | [Detection Methods]
T,NMR,Rotation | [BRN ]
1727869 | [CAS DataBase Reference]
2488-15-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [F ]
9-23 | [HS Code ]
29309090 |
| Hazard Information | Back Directory | [Chemical Properties]
white to off-white microcrystalline powder | [Uses]
N-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 suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
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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