D-2-Bromophenylalanine
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D-2-Bromophenylalanine
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CAS No:
267225-27-4
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Formula:
C9H10BrNO2
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Chemical Name:
D-2-Bromophenylalanine
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Synonyms:
H-D-PHE(2-BR)-OH;H-O-BROMO-D-PHE-OH;D-2-BROMOPHE;D-2-BROMOPHENYLALANINE;2-BROMO-D-PHENYLALANINE;(R)-2-AMINO-3-(2-BROMO-PHENYL)-PROPIONIC ACID;RARECHEM BK PT 0040;(2R)-2-amino-3-(2-bromophenyl)propanoic acid
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CAS No:
Characteristics
63.3
-0.7
White to off-white Powder
1.6±0.1 g/cm3
363.2°C at 760 mmHg
173.4±25.1 °C
1.609
Store at -15°C
6.53E-06mmHg at 25°C
D-2-Bromophenylalanine Use and Manufacturing
General procedure: To a 5 mL vial equipped with a magnetic stirrer bar were added 3-cyclohexyl-2-oxopropanoic acid (1j) (0.0510 g, 0.30 mmol), 2, 2-diphenylglycine (2) (0.0681 g, 0.30 mmol), chiral pyridoxamine 6g (0.0195 g, 0.030 mmol), and MeOH-H2O (8:2) (3.0 mL). The mixture was stirred at 20 °C for 3 days. The reaction mixture was transferred to a 25 mL round-bottom flask and MeOH was added until all the solid was dissolved. Then silica gel (0.50 g) was added. After removal of the solvent in vacuo at 20 °C, the resulting residue was submitted to column chromatography on silica gel (EtOH/ethyl acetate/25-28percent ammonia solution =100:58:16) to give compound 3j (0.0401 g, 78percent yield, 52percent ee) as a white solid. The enantiomeric excesses of 3b-k were deteremined by HPLC analysis after being converted to N-benzoyl methyl esters by treatment with thionyl chloride in methanol and subsequent reaction benzoyl chloride.7 The enantiomeric excess of 3a was deteremined by HPLC analysis after being converted to its methyl ester by treatment with CH2N2 in methanol.
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