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CAS No. : | 32675-71-1 | MDL No. : | |
Formula : | C19H14N2O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 334.33 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
100% | RG108 was obtained by the reaction of MSB with L-tryptophan under basic conditions (Na2CO3) in water/acetonitrile, acidification with 2N HCl, extraction in ethyl acetate and evaporation of the solvent with an excellent yield of 100%. The pure yellow powder was analysed by mass spectrometry (ESI) and 1H- and 13C-NMR to confirm the structure of RG108. | |
(i) (S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-(1H-indoI-3-yl)-propionic acid (50) A mixture of L-tryptophan (4g, 19.5mmol), methyl 2-((succinimidooxy)carbonyl)benzoate (5.3g, 19mmol) and potassium carbonate (0.69 g, 5 mmol) in dimethyiformamide was heated to 100 C for 3 hours. The reaction was acidified with 2 M hydrochloric acid and extracted with ethyl acetate. The organics were washed with brine, dried (MgSO4) and evaporated in vacuo to afford the title compound as a yellow solid, which was purified by HPLC. LCMS (LCMS 1) m/z: 335 [M+H]+; RT 5.55 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In DCM; at 20℃; for 3h; | A suspension of (S)-2-(1 ,3-dioxo-1 ,3-dihydro-isoindol-2-yl)-3-(1 H-indol-3-yl)-propionic acid (50) (4.5g, 13.5mmol) and Lambda/-(3-dimethy.aminopropyl)-Lambda/'-ethylcarbodiimide hydrochloride (2.6g, 13.5mmol) in DCM was treated with N.O-dimethyl hydroxylamine hydrochloride (1.3g, 13.5mmol) and triethylamine (3.7ml, 127mmol) and the resulting brown solution was stirred at room temperature for 3 hours. The crude reaction mixture was then washed with brine, dried (MgSO4) and concentrated in vacuo. The crude mixture was purified by preparative HPLC. LCMS (LCMS 1) m/z 378.4 [M+H]+, RT 5.75min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dicyclohexyl-carbodiimide; In acetonitrile; at 0℃; for 5h; | A solution of (S)-2-(1,3-Dioxo-1 ,3-dihydro-isoindol-2-yl)-3-(1H-indol-3-yl)-propionic acid (50) (1.7g, 5mmol), N-hydroxysuccinimide (0.6g, 5.2mmol) and dicyclohexylcarbodiimide (1.1g, 5mmol) was stirred at O0C in acetonitrile (35ml) for 5 hours. The resulting urea was filtered off and the solvent evaporated in vacuo to afford the title compound as a white solid. NMR 1H ppm: 8.01 (br, 1H), 7.76 (m, 2H), 7.66 (m, 2H), 7.28 (S1 1H), 7.05 (m, 3H), 5.60 (dd, 1 H), 3.80 (m, 2H)1 2.01 (s, 3H); 13C ppm: 168.43, 166.80, 165.02, 136.04, 134.24, 131.47, 126.96, 123.67, 123.01 , 122.27,119.73, 118.41 , 111.18, 109.76, 50.72, 25.58, 24.93; LCMS (LCMS1) m/z 431.7 [M+H]+, RT 5.31 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of (S)-2-(1 ,3-dioxo-1 ,3-dihydro-isoindol-2-yl)-3-(1Hindol-3-yl)-propionic acid (61) (1 g, 3 mmol) in acetonitrile (15 ml) was added 1 ,3-dicyclohexyldicarbodiimide (DCC) (619 mg, 3 mmol), 1-hydroxybenzotriazole hydrate (HOBT) (405 mg, 3 mmol) and the mixture stirred at 00C for 2 hours. The reaction mixture was filtered and to the yellow filtrate was added hydroxyiamine hydrochloride (208 mg, 3 mmol), triethylamine (364 mg, 3.6 mmol) and the reaction stirred at room temperature overnight. The solution was acidified to pH1 (1 M HCI) and diluted with ethylacetate (approx. 50ml). The solution was washed with 1 M HCI (2 x 30 ml), brine (30 ml), and the organics collected, dried (MgSO4), concentrated in vacuo to afford a yellow solid. The residue was purified by preparative HPLC to afford the title compound. LCMS m/z: 350 [M+1]; RT 5.21 min. EPO <DP n="55"/> |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; hydrazine; In acetonitrile; at 0℃; for 5h; | A solution of (S)-2-(1,3-dioxo-1 ,3-dihydro-isoindol-2-yl)-3-(1/-/-indol-3-yl)-propionic acid (50) (0.18g, 0.55mmol), Lambda/-(3-dimethylaminopropyl)-Lambda/-ethylcarbodiimide hydrochloride (0.11g, 0.55mmol), hydrazine (0.017ml, 0.55mmol) and triethylamine (0.21ml, 1.5mmol) were stirred at O0C in acetonitrile (35ml) for 5 hours. The crude reaction was washed EPO <DP n="51"/>with brine, dried (MgSO4) and concentrated in vacuo. The crude mixture was purified by preparative HPLC. LCMS (LCMS1) m/z 349.4 [IvHH]+; RT 5.12 min, purity 89.02%. |