BOC-L-4-Fluorophe
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BOC-L-4-Fluorophe
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CAS No:
41153-30-4
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Formula:
C14H18FNO4
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Chemical Name:
BOC-L-4-Fluorophe
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Synonyms:
N-alpha-t-Butyloxycarbonyl-4-fluoro-L-phenylalanine;(S)-N-BOC-4-FLUOROPHENYLALANINE, 95%, 98% EE;(S)-N-BOC-4-Fluorophenylalanine, 98% ee;Boc-L-4-Fluoro-phe-OH;L-Phenylalanine,N-[(1,1-diMethylethoxy)carbonyl]-4-fluoro-;Boc-L-Phe(4-F) -OH Boc-4-Fluoro-L-Phenylalanine;N-Boc-4-fluoro-L-phenylalanine Boc-Phe(4-F)-OH;Boc-4-fluoro-L-phenylalanine Boc-p-fluoro-Phe-OH
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CAS No:
Characteristics
75.6
1.9
White Powder
1.1918 (estimate)
83-86 °C
431.2±40.0 °C(Predicted)
214.6±27.3 °C
1.517
Keep Cold
8 º (c=1,MeOH)
3.87±0.10(Predicted)
Sealed in dry,2-8°C
Safety Information
NONH for all modes of transport
3
Xi
24/25
Xi
Irritant/Keep Cold
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
BOC-L-4-Fluorophe Use and Manufacturing
A solution of L-4F-Phe-COOH 1.97 g (10 mmol) in a mixture of dioxane (20 mL), water (20 mL) and 1 M NaOH (10 mL) was stirred and cooled in an ice-water bath. Ditert-butylpyrocarbonate 2.4 g (11 mmol) was added and stirring was continued at room temperature for 6 h. Then the solution was concentrated in vacuum to about 15—20 mL, cooled in an ice water bath, covered with a layer of ethyl acetate (about 30 mL) and a dilute solution of KHSO4 was added to acidify (pH 2—3). The aqueous phase was extracted with ethyl acetate and this operation was done three times. The ethyl acetate extracts were collected and dried over anhydrous Na2SO4 and evaporated in a vacuum. The pure material was obtained as a waxy solid.Yield: 2.115 g (7.25 mmol, 72.5percent)1H NMR (DMSO-d6, 400 MHz, ppm): 12.60 [s, 1H COOH], 7.29-7.25 & 7.11-7.07 [m, 4H, Aromatic protons], 4.10-3.00 [m, 1H, CaH 4F Phe], 3.03-2.77 [m, 2H, CI3H4F Phe], 1.33 [s, 9H, Boc].MALDI-TOF (matrix: a-cyano-4-hydroxy cinnamic acid (CHCA)) :mlz= [M+H] + 284.12 (calculated), 284.29 (observed), [M+Na]+ 306.11 (calculated), 306.25 (observed).
Boc-Phe(4-F)-OH, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.
Computed Properties
Molecular Weight:283.29
XLogP3:1.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:6
Exact Mass:283.12198622
Monoisotopic Mass:283.12198622
Topological Polar Surface Area:75.6
Heavy Atom Count:20
Complexity:346
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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