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Boc-N-Me-Val-OH

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CAS:45170-31-8
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  • 2024-04-28
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  • Boc-N-Me-Val-OH
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  • $65.00 / 1KG
  • 2024-01-02
  • CAS:45170-31-8
  • Min. Order: 1KG
  • Purity: 0.99
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Boc-N-Me-Val-OH Basic information
Product Name:Boc-N-Me-Val-OH
Synonyms:BOC-N-METHYL-L-VAL-OH;N-ALPHA-TERT-BUTYLOXYCABONYL-N-ALPHA-METHYL-L-VALINE;NALPHA-tert-Butoxycarbonyl-N-methyl-L-valine;N-[(tert-Butoxy)carbonyl]-N-methyl-L-valine;(S)-2-((tert-Butoxycarbonyl)(Methyl)aMino)-3-Methylbutanoic acid;Boc-N-Me-Val-OH >=99.0% (TLC);Boc-N-Me-L-Val-OH;(2S)-2-[[(tert-Butoxy)carbonyl](methyl)amino]-3-methylbutanoic acid
CAS:45170-31-8
MF:C11H21NO4
MW:231.29
EINECS:
Product Categories:amino acids;Valine [Val, V];N-Methyl Amino Acids;Boc-Amino acid series
Mol File:45170-31-8.mol
Boc-N-Me-Val-OH Structure
Boc-N-Me-Val-OH Chemical Properties
Melting point 45-60°C
Boiling point 322.4±21.0 °C(Predicted)
alpha -94 º (c=0.5% in ethanol)
density 1.069±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
pka4.03±0.10(Predicted)
form Solid
color Off-White
optical activity[α]20/D 94±3°, c = 0.5% in ethanol
BRN 2646180
InChIInChI=1S/C11H21NO4/c1-7(2)8(9(13)14)12(6)10(15)16-11(3,4)5/h7-8H,1-6H3,(H,13,14)/t8-/m0/s1
InChIKeyXPUAXAVJMJDPDH-QMMMGPOBSA-N
SMILESC(O)(=O)[C@H](C(C)C)N(C(OC(C)(C)C)=O)C
CAS DataBase Reference45170-31-8(CAS DataBase Reference)
Safety Information
WGK Germany 3
HazardClass IRRITANT
HS Code 29225090
MSDS Information
ProviderLanguage
SigmaAldrich English
Boc-N-Me-Val-OH Usage And Synthesis
Chemical PropertiesWhite powder
UsesN-Boc-N-methyl-L-valine (Boc-N-Me-Val-OH) is an amino acid derived compound that functions as a useful pharmaceutical intermediate and also employed as a reagent used in organic synthesis. It is used in the synthesis of lactam analog of actinomycin D, a potential antitumor chemotherapeutic agent. It is also used to N-tert-Butoxycarbonyl-N-methyl-L-valine 4-ethynylanilide with 4-ethynylaniline[1].
SynthesisTo a solution of N-BOC-valine 1 (217 mg, 1 mmol) and iodomethane(1.42 g, 10 mmol) in anhydrous tetrahydrofuran (THF,20 mL) was added neat sodium hydride (240 mg, 10 mmol). The reaction mixture was stirred at room temperature for 24 hours. The mixture was then quenched with water (30 mL). The reaction mixture was extracted with ethyl acetate (EtOAc, 2 15 mL) and the aqueous solution was acidified to pH 3, after which it was extracted with EtOAc (3 20 mL). The combined organic phase was dried over anhydrous Na2SO4 and evaporated to afford the corresponding Boc-N-Me-Val-OH (thick colorless oil), 99% yield.
Boc-N-Me-Val-OH
References[1] Masashi Shiotsuki. “Molecular weight dependence of helical conformation of amino acid-based polyphenylacetylenes.” Journal of Polymer Science Part A: Polymer Chemistry 49 22 (2011): 4921–4925.
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