Boc-3,4-difluoro-DL-phenylalanine
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Boc-3,4-difluoro-DL-phenylalanine

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A reactant in the preparation of amino acid derivatives as melanocortin receptor ligands.

Category
BOC-Amino Acids
Catalog number
BAT-001385
CAS number
1214041-87-8
Molecular Formula
C14H17F2NO4
Molecular Weight
301.30
IUPAC Name
3-(3,4-difluorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Synonyms
Boc-3,4-difluoro-DL-phenylalanine; Boc-3,4-difluoro-DL-Phe-OH; (RS)-Boc-2-amino-3-(3,4-difluorophenyl)propionic acid
Purity
≥ 99% (HPLC)
Melting Point
103-110°C
Storage
Store at 2-8 °C
InChI
InChI=1S/C14H17F2NO4/c1-14(2,3)21-13(20)17-11(12(18)19)7-8-4-5-9(15)10(16)6-8/h4-6,11H,7H2,1-3H3,(H,17,20)(H,18,19)
InChI Key
CYAOPVHXASZUDE-UHFFFAOYSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC1=CC(=C(C=C1)F)F)C(=O)O
1. Synthesis of 1-Boc-3-fluoroazetidine-3-carboxylic acid
Eva Van Hende, Guido Verniest, Frederik Deroose, Jan-Willem Thuring, Gregor Macdonald, Norbert De Kimpe J Org Chem. 2009 Mar 6;74(5):2250-3. doi: 10.1021/jo802791r.
Synthetic strategies toward 3-fluoroazetidine-3-carboxylic acid, a new cyclic fluorinated beta-amino acid with high potential as building block in medicinal chemistry, were evaluated. The successful pathway includes the bromofluorination of N-(diphenylmethylidene)-2-(4-methoxyphenoxymethyl)-2-propenylamine, yielding 1-diphenylmethyl-3-hydroxymethyl-3-fluoroazetidine after reduction of the imino bond, ring closure, and removal of the 4-methoxybenzyl group. Changing the N-protecting group to a Boc-group allows further oxidation to 1-Boc-3-fluoroazetidine-3-carboxylic acid, a new fluorinated heterocyclic amino acid.
2. Inhibitor mediated protein degradation
Marcus J C Long, Deviprasad R Gollapalli, Lizbeth Hedstrom Chem Biol. 2012 May 25;19(5):629-37. doi: 10.1016/j.chembiol.2012.04.008.
The discovery of drugs that cause the degradation of their target proteins has been largely serendipitous. Here we report that the tert-butyl carbamate-protected arginine (Boc(3)Arg) moiety provides a general strategy for the design of degradation-inducing inhibitors. The covalent inactivators ethacrynic acid and thiobenzofurazan cause the specific degradation of glutathione-S-transferase when linked to Boc(3)Arg. Similarly, the degradation of dihydrofolate reductase is induced when cells are treated with the noncovalent inhibitor trimethoprim linked to Boc(3)Arg. Degradation is rapid and robust, with 30%-80% of these abundant target proteins consumed within 1.3-5 hr. The proteasome is required for Boc(3)Arg-mediated degradation, but ATP is not necessary and the ubiquitin pathways do not appear to be involved. These results suggest that the Boc(3)Arg moiety may provide a general strategy to construct inhibitors that induce targeted protein degradation.
3. Synthesis of Simple 3,3-Diarylazetidines from N-Boc-3-arylazetidinols Using Friedel-Crafts Arylation Conditions
Madhurima Das, Amber Weissenfluh, Nam Ly, Mark L Trudell J Org Chem. 2020 Jun 19;85(12):8209-8213. doi: 10.1021/acs.joc.0c00454. Epub 2020 Jun 7.
A synthesis of 3,3-diarylazetidines from N-Boc-3-aryl-3-azetidinols using Friedel-Crafts arylation conditions with AlCl3 is described. A series of substituted diarylazetidines were readily prepared and isolated as the oxalate salts in high yield and high purity. The 3,3-diarylazetidine oxalates were then easily converted into N-alkyl and N-acyl analogues (RX, NaHCO3/DMF/100 °C) in high overall yields.
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