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Chemical Structure| 2389-48-2 Chemical Structure| 2389-48-2
Chemical Structure| 2389-48-2

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H-Lys(Boc)-OMe·HCl is a lysine derivative, commonly used in peptide synthesis and drug development.

Synonyms: H-Lys(Boc)-OMe hydrochloride

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Product Details of H-Lys(Boc)-OMe·HCl

CAS No. :2389-48-2
Formula : C12H25ClN2O4
M.W : 296.79
SMILES Code : O=C(OC)[C@@H](N)CCCCNC(OC(C)(C)C)=O.[H]Cl
Synonyms :
H-Lys(Boc)-OMe hydrochloride
MDL No. :MFCD00076959
InChI Key :NANRHOPPXCBHGI-FVGYRXGTSA-N
Pubchem ID :16218818

Safety of H-Lys(Boc)-OMe·HCl

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of H-Lys(Boc)-OMe·HCl

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 2389-48-2 ]

[ 2389-48-2 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 1738-87-0 ]
  • [ 2389-48-2 ]
  • [ 37169-25-8 ]
  • 2
  • [ 24424-99-5 ]
  • [ 2389-48-2 ]
  • [ 2483-48-9 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃; EXAMPLE 1Preparation of N-[(5S)-5- { [(4-aminophenyl)sulfonyl](3-methylbutyl)amino}hydroxyhexyl]-Na-(metl oxycarbonyl)- -phenyl-L-phenylalaninamideStep 1 : preparation of tert-butyl {(25)-6-[(teri-butoxycarbonyl)amino]-l-hydroxyhexan-2- yl} carbamate; To a solution of methyl N^-(½ri-butoxycarbonyl)-L-lysmate hydrochloride(5.0 g, 16.85 mmol) and triethylamine (2.82 mL, 20.22 mol) in dic oromethane (84 mL) was added a solution of di-tert-butyl dicarbonaie (3.7 g, 1 .85 mmol) in dichloromethane(10 mL). The reaction mixture was stirred at room temperature overnight, poured into 10% HSO4, and extracted with dichloromethane (2X). The combined organics were washed with saturated aqueous aHC03, brine, dried over MgS04, filtered and concentrated to yield 6.1 g of methyl N^^-bis(tert-bntoxy ^b ny[)-L-lys atQ as an off white solid. MS'.M+Na = 383. The residue was dissolved in THF (85 mL), and the solution was cooled to 0C. 2 M of L1BH4 in THF (12.69 mL, 25.4 mmol) was slowly added. The reaction mixture was stirred at room temperature for 1 hour, then at 50 C for 1 hour. It was then cooled to 0C and methanol was carefully added (1.5 mL). The reaction temperature was allowed to stand at room temperature, and 1 N NaOH (2 mL) was added followed by the addition of brine. The reaction mixture was vigorously stirred at room temperature for 30 min, then extracted with EtOAc (2X). The combined organics were washed with brine, dried over gS04, filtered and concentrated to yield 5.8 g of bis-Boc-lysinol material as a colorless viscous oil. MS (M+Na) = 355.
  • 3
  • [ 2389-48-2 ]
  • [ 117833-18-8 ]
  • methyl (2S,5S)-3,6-diaza-2-[4-(tert-butoxycarbonyl)aminobutyl]-5-(tert-butoxycarbonyl)methyl-4,7-dioxooctanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 12h;Inert atmosphere; Sealed tube; General procedure: The acid, HOBt, EDCI, and the amine hydrochloride were placed in a flask, and then placed under high vacuum to dry. The vessel was then sealed and flushed with N2. Anhydrous DMF and DIPEA were added at rt and the solution was allowed to stir at rt for 12h (in cases where the amine was present as the free base, DIPEA was not necessary and therefore excluded). The reaction was diluted with water until precipitation occurred (30mL). The aqueous mixture was extracted with CH2Cl2 (3×50mL) and the combined CH2Cl2 extracts were thoroughly washed with water (3×30mL) dried (MgSO4) and concentrated in vacuo yield the desired amide.
  • 4
  • [ 402-69-7 ]
  • [ 2389-48-2 ]
  • C18H26FN3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% [0309] To a solution of compound 28.1 (366.07 mg, 2.6 mmol, 1.1 equivalent) in DMF (15 mL) was added HOBt (350.77 mg, 2.6 mmol, 1.1 equivalent) and EDCI (497.65 mg, 2.60 mmol, 1.1 equivalent). The mixture was stirred at 0 CC for 1 hr. Then to the mixture was added compound 26.1 (700 mg, 2.36 mmol, 1 equivalent, HC1) and DIEA (1.22 g, 9.44 mmol, 1.65 mL, 4 equivalent): the mixture was stirred at 25 °C for 14 hours. The reaction mixture was quenched by addition hLO (30 mL) and extracted with ethyl acetate (30xmL x 3). The combined organic layers were washed with saturated brine (5 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Si02, DCM: MeOH = 10: 1) to give compound 28.2 (750 mg, 1.96 mmol, 83percent yield) as yellow oil; LCMS [M + H - Boc]+: 384; RT = 0.817 min. FontWeight="Bold" FontSize="10" H NMR (400 MHz, CHLOROFORMS) delta ppm 1.42 (s, 1 1 H), 1.53 (br d, J=6.17 Hz, 2 H), 1.65 (s, 1 H), 1.75 - 2.05 (m, 2 H), 3.12 (br d, J=6.17 Hz, 2 H), 3.78 (d, J=0.66 Hz, 3 H), 4.57 (br s, 1 H), 4.67 - 4.89 (m, 1 H), 6.97 - 7.18 (m, 1 H), 7.87 - 8.03 (m, 1 H), 8.05 - 8.22 (m, 2 H).
 

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