Fmoc-N-methyl-L-phenylalanine Chemical Properties

Melting point:

132.0 to 136.0 °C

Boiling point:

595.4±39.0 °C(Predicted)

Density 

1.260±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Soluble in DMF. (0.3gram in 2ml)

pka

3.78±0.10(Predicted)

form 

Powder

color 

Off-white

optical activity

[α]20/D 55.0±3°, c = 1% in DMF

BRN 

4768138

InChI

InChI=1S/C25H23NO4/c1-26(23(24(27)28)15-17-9-3-2-4-10-17)25(29)30-16-22-20-13-7-5-11-18(20)19-12-6-8-14-21(19)22/h2-14,22-23H,15-16H2,1H3,(H,27,28)/t23-/m0/s1

InChIKey

GBROUWPNYVBLFO-QHCPKHFHSA-N

SMILES

C(O)(=O)[C@H](CC1=CC=CC=C1)N(C(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O)C

CAS DataBase Reference

77128-73-5(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

2924 29 70

HazardClass 

IRRITANT

MSDS

• Language:English Provider:SigmaAldrich

Fmoc-N-methyl-L-phenylalanine Usage And Synthesis

Chemical Properties

White to off-white powder

Uses

N-Fmoc-N-methyl-L-phenylalanine is used in agrochemical, pharmaceutical and dyestuff field.

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

Fmoc-phenylalanyl oxazolidinone (4.60 g, 11.6 mmol) was dissolved in chloroform (58 mL). To this solution, trifluoroacetic acid (2.68 mL, 34.8 equiv) and triethylsilane (5.56 mL, 34.8 equiv) were added sequentially. The reaction mixture was stirred at room temperature until the reaction was complete (24-72 hours). Upon completion of the reaction, the solution was concentrated and subsequently partitioned between ether and saturated sodium bicarbonate solution. The aqueous phase was combined, acidified to pH 2 with 5 M hydrochloric acid and extracted with ethyl acetate. The organic phase was collected, dried with anhydrous magnesium sulfate and concentrated to give a dark yellow oily product. The crude product was dissolved in dichloromethane and repeatedly evaporated to yield Fmoc-N-methylphenylalanine as a brown solid (3.73 g, 80% yield): melting point 106-107 °C; low-resolution mass spectrometry (ESI) m/z [M + H]+ 402.1 (100%); 1H NMR (300 MHz, CDCl3) δH (ppm) (rotated isomer ) 7.74 (2H, d, J = 7.5 Hz, ArH), 7.49 (1H, d, J = 7.8 Hz, ArH), 7.43 (1H, t, J = 6.9 Hz, ArH), 7.37 (2H, t, J = 7.5 Hz, ArH), 7.25-7.21 (6H, m, ArH), 6.95 (1H, d, J = 6.3 Hz , ArH), 4.89 (1H, dd, J = 5.1, 11.1 Hz, NCHCOOH), 4.59-4.53 (1H, m, (Ar)2CHCH2), 4.38 (2H, d, J = 14.4 Hz, CHCH2O), 3.41-3.35 (1H, m, CHCHHAr), 3.16-3.08 (1H m, CHCHHAr), 2.77 (3H, s, NCH3), 2.75 (3H, s, NCH3) (1H NMR data are consistent with literature reports); 13C NMR (75 MHz, CDCl3) δC (ppm) 175.5, 156.5, 143.4, 140.9, 136.4, 128.4, 128.3, 127.3, 126.7, 126.5, 124.6, 124.3, 119.6, 67.6, 60.7, 46.7, 34.3, 32.3.

IC 50

Plasmodium

References

[1] Journal of Organic Chemistry, 2005, vol. 70, # 17, p. 6918 - 6920
[2] European Journal of Organic Chemistry, 2013, # 21, p. 4509 - 4513
[3] Tetrahedron, 2014, vol. 70, # 14, p. 2351 - 2358
[4] Tetrahedron Letters, 2006, vol. 47, # 11, p. 1691 - 1694
[5] Angewandte Chemie - International Edition, 2008, vol. 47, # 14, p. 2595 - 2599

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