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)

form 

Solid

pka

4.03±0.10(Predicted)

color 

Off-White

optical activity

[α]20/D 94±3°, c = 0.5% in ethanol

BRN 

2646180

InChI

InChI=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

InChIKey

XPUAXAVJMJDPDH-QMMMGPOBSA-N

SMILES

C(O)(=O)[C@H](C(C)C)N(C(OC(C)(C)C)=O)C

CAS DataBase Reference

45170-31-8(CAS DataBase Reference)

Safety Information

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29225090

MSDS

• Language:English Provider:SigmaAldrich

Boc-N-Me-Val-OH Usage And Synthesis

Chemical Properties

White powder

Uses

N-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].

Synthesis

To 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.

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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