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ChemicalBook--->CAS DataBase List--->77128-73-5

77128-73-5

77128-73-5 Structure

77128-73-5 Structure
IdentificationMore
[Name]

Fmoc-N-methyl-L-phenylalanine
[CAS]

77128-73-5
[Synonyms]

FMOC-L-MEPHE-OH
FMOC-MEPHE-OH
FMOC-N-ALPHA-METHYL-L-PHENYLALANINE
FMOC-N-ME-L-PHE-OH
FMOC-N-ME-PHENYLALANINE
FMOC-N-ME-PHE-OH
FMOC-N-METHYL-L-PHENYLALANINE
N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-N-ALPHA-METHYL-L-PHENYLALANINE
N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-N-ALPHA-METHYL-L-PHENYLALANINE
N-ALPHA-FMOC-N-ALPHA-METHYL-L-PHENYLALANINE
FMOC-N-ME-PHE 98.5+%
N-(9-Fluorenylmethyloxycarbonyl)-N-methyl-L-phenylalanine
FMOC-N-METHYL-L-PHENYLALANINE LIQUID
[Molecular Formula]

C25H23NO4
[MDL Number]

MFCD00151938
[Molecular Weight]

401.45
[MOL File]

77128-73-5.mol
Chemical PropertiesBack Directory
[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)
[form ]

Powder
[pka]

3.78±0.10(Predicted)
[color ]

Off-white
[Optical Rotation]

[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 DataBack Directory
[Safety Statements ]

S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
[WGK Germany ]

3
[HS Code ]

2924 29 70
[HazardClass ]

IRRITANT
Hazard InformationBack Directory
[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]

9H-Fluoren-9-ylmethyl(4S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylate

84000-03-3

Fmoc-N-methyl-L-phenylalanine

77128-73-5

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
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

77128-73-5(sigmaaldrich)
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