| Identification | More | [Name]
BOC-L-3-FLUOROPHENYLALANINE | [CAS]
114873-01-7 | [Synonyms]
BOC-3-FLUORO-L-PHE
BOC-3-FLUORO-L-PHENYALANINE
BOC-3-FLUORO-L-PHENYLALANINE
BOC-L-3-FLUOROPHE
BOC-L-3-FLUOROPHENYLALANINE
BOC-L-PHE(3-F)-OH
BOC-M-FLUORO-PHE-OH
BOC-O-FLUORO-L-PHENYALANINE
BOC-PHE(3-F)-OH
BOC-PHE(M-F)-OH
BOC-(S)-2-AMINO-3-(3'-FLUOROPHENYL)PROPANOIC ACID
L-3-FLUOROPHENYLALANINE, BOC PROTECTED
N-ALPHA-T-BUTOXYCARBONYL-3-FLUORO-L-PHENYLALANINE
N-ALPHA-T-BUTYLOXYCARBONYL-L-3-FLUOROPHENYLALANINE
N-ALPHA-TERT-BUTYLOXYCARBONYL-3-FLUORO-L-PHENYLALANINE
N-TERT-BUTOXYCARBONYL-3-FLUOROPHENYL-L-ALANINE
RARECHEM BK PT 0026
(S)-2-TERT-BUTOXYCARBONYLAMINO-3-(3-FLUORO-PHENYL)-PROPIONIC ACID
(S)-N-BOC-3-FLUOROPHENYLALANINE
L-3-Fluorophenylalanine, N-BOC protected | [Molecular Formula]
C14H18FNO4 | [MDL Number]
MFCD00672522 | [Molecular Weight]
283.3 | [MOL File]
114873-01-7.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white crystalline powder | [Melting point ]
75-80 °C
| [Boiling point ]
425.0±40.0 °C(Predicted) | [density ]
1.1918 (estimate) | [storage temp. ]
Keep Cold | [solubility ]
slightly sol. in Ethanol | [form ]
powder to crystal | [pka]
3.82±0.10(Predicted) | [color ]
White to Almost white | [Optical Rotation]
[α]20/D +6.5±1°, c = 1% in methanol | [BRN ]
5347375 | [InChI]
InChI=1S/C14H18FNO4/c1-14(2,3)20-13(19)16-11(12(17)18)8-9-5-4-6-10(15)7-9/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m0/s1 | [InChIKey]
FPCCREICRYPTTL-NSHDSACASA-N | [SMILES]
C(O)(=O)[C@H](CC1=CC=CC(F)=C1)NC(OC(C)(C)C)=O | [CAS DataBase Reference]
114873-01-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [Hazard Note ]
Irritant/Keep Cold | [HazardClass ]
IRRITANT | [HS Code ]
2922498590 |
| Hazard Information | Back Directory | [Chemical Properties]
off-white crystalline powder | [Uses]
peptide synthesis | [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
The general procedure for the synthesis of (S)-2-((tert-butoxycarbonyl)amino)-3-(3-fluorophenyl)propionic acid from di-tert-butyl dicarbonate and L-3-fluorophenylalanine was as follows: first, L-2-amino-3-(3-fluorophenyl)-propionic acid (20.0 g, 110 mmol, 1 eq.) was dissolved in water (100 mL) and sodium carbonate (16.2 g. 153 mmol, 1.4 eq.) in water (40 mL). Subsequently, 1,4-dioxane (100 mL) was added and the mixture was cooled to 0 °C. Di-tert-butyl dicarbonate was added with stirring and the reaction mixture was then stirred at room temperature for 5 hours. After the reaction was complete, the dioxane was removed by evaporation. Water (125 mL) was added to dilute the reaction mixture, which was subsequently washed with ether (2 x 100 mL). The aqueous phase was acidified with 10% citric acid and then extracted with ethyl acetate (2 x 300 mL). The organic phases were combined, washed sequentially with water (2×150 mL) and brine (150 mL), dried with anhydrous sodium sulfate, and concentrated to afford the target product (S)-2-((tert-butoxycarbonyl)amino)-3-(3-fluorophenyl)propionic acid as a colorless viscous oil, which slowly solidified after standing (31 g, quantitative yield). The 1H NMR (CDCl3) data of the product were as follows: δ 7.33-7.26 (m, 1H), 7.00-6.91 (m, 3H), 4.96 (s, 1H), 4.62 (bs, 1H), 3.23 (dd, J = 14, 5.3Hz, 2H), 1.44 (s, 9H). Elemental analysis (C14H18NO4F) calculated values: C, 59.36; H, 6.40; N, 4.94. measured values: C, 59.29; H, 6.34; N, 4.90. | [References]
[1] Patent: WO2005/26114, 2005, A1. Location in patent: Page/Page column 85
[2] Patent: WO2005/26114, 2005, A1. Location in patent: Page/Page column 102
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 13, p. 2090 - 2099 |
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