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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 943-80-6 |
Formula : | C9H12N2O2 |
M.W : | 180.20 |
SMILES Code : | O=C(O)[C@@H](N)CC1=CC=C(N)C=C1 |
MDL No. : | MFCD00069927 |
InChI Key : | CMUHFUGDYMFHEI-QMMMGPOBSA-N |
Pubchem ID : | 151001 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With barium sulfate; hydrogen; palladium; | To a solution of Ap, a mixture of 8 g L-4-nitrophenylalanine (38 mmol) and 0.8 g barium sulfate was put in a 250 mL three-necked flask while adding the gas of hydrogen to do the hydrogenation for 4 h. The reaction mixture was filtered and concentrated to crystallization. The productions were washed with water, dried and evaporated. Finally, we added 5.9 g white powder and the yield was 87%(Fig. 1F) [19]. |
85% | With rosenmund catalyst; hydrogen; In water; at 20℃; for 3h; | A mixed solution of concentrated HNO3 (60%) and concentrated H2SO4 (1.4:1.1 v/v) was prepared and chilled to 10 C. Then, a portion of this solution (3.5 mL) was added dropwise under stirring to a solution of L-phenylalanine (4.139 g, 25.1 mmol) in H2SO4 (98%, 12.5 mL). The reaction mixture was stirred at 10 C for 2.5 h. The reaction solution was then adjusted to pH 5 with NH4OH. The pale yellow precipitate formed was collected by filtration, washed with a small volume of water and CH3CN, and then dried to yield 4-nitro-L-phenylalanine as a yellow powder (4.748 g, 90%). 4-Nitro-L-phenylalanine (2.006 g, 9.54 mmol) was suspended in water (35 mL) and subjected tohydrogenation at room temperature for 3 h in the presence of 0.2 g of 5% palladium-barium sulfate.The catalyst was filtered through a Celite pad, and the pale brown filtrate was concentrated. Theresidue was washed with CH3CN to afford a pale brown mass (1.460 g, 85%). No further purificationwas performed for the following step. The 4-amino-L-phenylalanine derivative (0.060 g, 0.33 mmol)was dissolved in 6N HCl (4 mL). Sodium nitrate in water (0.030 g/0.5 mL) was added at 0 C. Thereaction mixture was stirred at the same temperature for 40 min and diluted with 6N HCl (0.25 mL).Subsequently, sodium azide in water (0.033 g/0.75 mL) was added at 0 C. The reaction mixture wasstirred at same temperature for 5 min, and then warmed to room temperature for 1 h, thenconcentrated. The residue was reprecipitated from CH3CN to afford a pure colorless amorphous mass(0.0435 g, 64%). Analytical and spectroscopic data were identical to those reported in the literature [10]. |