D-Phenylalanine methyl ester hydrochloride Chemical Properties

Melting point:

159-163 °C(lit.)

refractive index 

-37.0 ° (C=2, EtOH)

storage temp. 

2-8°C

solubility 

Soluble in Ethanol and Methanol.

form 

Powder or Crystalline Powder

color 

White to off-white

InChI

InChI=1/C10H13NO2.ClH/c1-13-10(12)9(11)7-8-5-3-2-4-6-8;/h2-6,9H,7,11H2,1H3;1H/t9-;/s3

InChIKey

SWVMLNPDTIFDDY-SBSPUUFOSA-N

SMILES

C1(C=CC=CC=1)C[C@@H](N)C(=O)OC.Cl |&1:7,r|

CAS DataBase Reference

13033-84-6(CAS DataBase Reference)

Safety Information

WGK Germany 

3

HS Code 

29224999

MSDS

• Language:English Provider:SigmaAldrich

D-Phenylalanine methyl ester hydrochloride Usage And Synthesis

Chemical Properties

White Solid

Uses

D-Phenylalanine Methyl Ester Hydrochloride is a compound useful in organic synthesis used in the preparation of amidines via copper-catalyzed three-component coupling of sulfonyl azides with alkynes and amines.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

Example 4: General procedure for the synthesis of D-phenylalanine methyl ester hydrochloride: anhydrous methanol (50 mL) was added to a 100 mL two-necked round-bottomed flask equipped with a reflux condenser and a dropping funnel, and the system was cooled to ice bath temperature. Acetyl chloride (3 mL) was slowly added dropwise through the dropping funnel.After 15 min, D-phenylalanine (3 g, 18.16 mmol) was added to the reaction system, followed by refluxing the reaction mixture at 70 °C overnight. Upon completion of the reaction, D-phenylalanine methyl ester hydrochloride was obtained by vacuum drying, and the product could be used for subsequent reactions without further purification. Procedure for synthesizing methyl phthalimide (D-NDI or NDI 3B): 1,4,5,8-naphthalenetetracarboxylic acid dianhydride (200 mg, 0.74 mmol) and D-phenylalanine methyl ester hydrochloride (322 mg, 1.49 mmol) were suspended in DMF (20 mL) in a 100 mL round-bottom flask. Triethylamine (0.6 mL) was added to the suspension under inert atmosphere. The reaction mixture was refluxed at 75 °C for 24 hours. At the end of the reaction, the solvent was removed by vacuum evaporation and the residue was purified by column chromatography (eluent: 1% chloroform solution in methanol) to afford the target product in 71% yield. Product characterization data: 1H NMR (400 MHz, CDCl3): δ8.63 (s, 4H), 7.1 (m, 10H), 6.02 (dd, 2H, J=4Hz, 4Hz), 3.77 (s, 6H), 3.73 (dd, 2H, J=8Hz, 4Hz), 3.50 (dd, 2H, J=12Hz, 4Hz). 13C NMR (400MHz, CDCl3): δ169.6, 162.4, 136.9, 131.3, 129.2, 128.5, 126.9, 126.8, 126.4, 54.9, 52.8, 34.9. mass spectra (EI): m/z=590.17 [M]+ (C34H26N2O8). Elemental analysis results: measured values: C, 69.10; H, 4.49; N, 4.78; calculated values: C, 69.15; H, 4.44; N, 4.74 (C34H26N2O8).

References

[1] Patent: WO2012/98439, 2012, A1. Location in patent: Page/Page column 17
[2] Patent: US6194409, 2001, B1

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