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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.
Boc-D-Leucine monohydrate is a non-natural isomer of D-leucine with N-Boc protection, acting as an autolysis inhibitor of lactic acid streptococcus and having strong antiepileptic effects.
Synonyms: (S)-2-((tert-Butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoic acid
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Batch number can be found on the product's label following the word 'Batch'.
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 3978-80-1 |
Formula : | C14H19NO5 |
M.W : | 281.30 |
SMILES Code : | OC(C=C1)=CC=C1C[C@@H](C(O)=O)NC(OC(C)(C)C)=O |
Synonyms : |
(S)-2-((tert-Butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoic acid
|
MDL No. : | MFCD00037179 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-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 |
---|---|---|
0.4 g | With lithium aluminium tetrahydride; In diethyl ether;Inert atmosphere; Reflux; | N-Boc-L-tyrosinol 4: 1?g of N-Boc-L-tyrosine (3.6?mmol) was dissolved under nitrogen in 80?mL of dry diethyl ether. Then lithium aluminium hydride (0.4?g, 0.01?mol) was added in portions. The suspension was heated to reflux overnight. After cooling to room temperature, ethyl acetate was added and the reaction mixture was poured carefully to concentrated sodium hydroxide solution while stirring. The organic layer was extracted with water and dried with sodium sulphate. 0.4?g oily material was obtained after removing the solvents. 1H NMR (400?MHz, CDCl3): delta 1.37 (9H, s), 2.69 (2H, d, J?=?6.51?Hz), 3.47 (1H, dd, J?=?5.27, 10.85?Hz), 3.57 (1H, dd, J?=?3.75, 10.85?Hz), 3.76 (1H, s), 5.06 (1H, d, J?=?7.75?Hz), 6.70 (2H, d, J?=?8.37?Hz), 6.97 (2H, d, J?=?8.37?Hz), 7.70 (1H, br s) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With triethylamine; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; acetonitrile; at 0℃; for 7h; | A solution of LDOPAmethyl ester hydrochloride 2 (0.27 g, 1.11 mmol) andN-(tert-butoxycarbonyl)-L-tyrosine (0.33 g, 1.16 mmol) inDMF (2.2 mL) and acetonitrile (9 mL) was cooled in ice.With stirring, triethylamine (0.16 mL, 1.11 mmol) was addedfollowed by dicyclohexylcarbodiimide (0.25 g, 1.11 mmol).After 7 h of continued stirring at 0 C, the reaction mixturewas cooled in the freezer overnight. The insoluble materialwas filtered off and washed with ethyl acetate. The combinedfiltrate was evaporated and the residue was dissolvedin ethyl acetate (40 mL) and water (25 mL). The organiclayer was washed successively with 25 mL portions of 0.5 NHCl, H2O, 0.5 N NaHCO3 and brine and dried over MgSO4.After filtration and concentration, the crude yellow solid wassubjected to silica chromatography (ethyl acetate/hexane =1:1, then 3:1) to afford a colorless amorphous mass (0.34 g,64%) 1H NMR (CD3OD): 1.34 (s, 3H), 2.67 (m, 1H), 2.90(m, 3H), 3.35 (s, 3H), 3.66 (s, 3H), 4.23 (t, J = 6.9 Hz, 1H),4.59 (t, J = 6.8 Hz, 1H), 6.48 (d, J = 7.9 Hz, 1H), 6.62 (s,1H), 6.68 (d, J = 7.9 Hz, 1H), 6.69 (d, J = 8.6 Hz, 2H), 7.01(d, J = 8.6 Hz, 2H); 13C NMR (CD3OD): 28.6, 37.9, 38.4,52.6, 55.2, 57.5, 80.7, 116.1. 116.3, 117.2, 121.7, 129.0,129.1, 131.3, 145.3, 146.2, 157.1, 157.5, 173.2, 174.2;HRMS (ESI): calcd. for C24H31N2O8 (M++H) 475.2080,found 475.2055; []D -2.1 (c 2.0, CH3OH). |