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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.
L-Cysteine HCl can increase glutathione levels and is important for lung and brain function and liver detoxification.
Synonyms: L-Cysteine(hydrochloride)
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CAS No. : | 52-89-1 |
Formula : | C3H8ClNO2S |
M.W : | 157.62 |
SMILES Code : | N[C@@H](CS)C(O)=O.[H]Cl |
Synonyms : |
L-Cysteine(hydrochloride)
|
MDL No. : | MFCD00064553 |
InChI Key : | IFQSXNOEEPCSLW-DKWTVANSSA-N |
Pubchem ID : | 60960 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P362-P403+P233-P405-P501 |
* 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 |
---|---|---|
98% | Triphenylmethanol (3.3 g, 12.7 mmol) was added to a solution of Cysteine chlorydrate (2 g, 12.7 mmol) in TFA (25 mL) and the mixture was stirred for 2 h. After cooling to 0 °C, NaOH 4N and diethyl ether (40 mL) were added until pH 4-5 and then 10percent sodium acetate aqueous solution was added until pH 5-6. The precipitated obtained was filtered, washed with fresh Et2O and finally dried to obtain the desired product (5 g, 98percent yield).1H NMR (DMSO): delta (ppm) 2.35-2.61 (m, 2H, CH2); 2.85-2.98 (m, 1H, CH); 7.2-7.45 (m, 15H, trityl-H).MALDI-TOF MS: m/z364.7 Da [M + H]+, C22H21NO2S, Mol. Wt.: 363.47. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In N,N-dimethyl-formamide; at 20℃; for 48h; | L-Cysteine hydrochloride (100 g, 0.634 mol) and trityl chloride (270 g, 0.969 mol) were stirred in DMF (400 mL) for 2 days at room temperature. A 10percent sodium acetate solution (3.5 L) was then added dropwise and the white precipitate which formed was filtered and washed with distilled water. Afterward, the residue was stirred in acetone at 50° C. for 30 min after which it was cooled to 0° C. and filtered. The precipitate was washed with a little acetone and diethyl ether and dried in vacuo. S-Trityl-L-cysteine 1b (205 g, 89percent) was obtained as a white powder. 1b: m.p. 192° C. (decomp). 1H NMR (DMSO-d6) delta 2.45 (dd, 1H, J=9 Hz, 12 Hz), 2.58 (dd, 1H, J=4.4 Hz, 12 Hz), 2.91 (m, 1H), 7.22-7.36 (m, 15H); 13C NMR (75.5 MHz, DMSO-d6): delta 33.8, 53.7, 66.4, 127.1, 127.8, 128.1, 128.4, 129.5, 144.5, 168.4. This material was directly used in the next step without further purification. |
89% | With sodium acetate; In N,N-dimethyl-formamide; at 20℃; for 48h; | L-Cysteine hydro-chloride (100 g, 0.634 mol) and trityl chloride (270 g, 0.969 mol) were stirred in DMF (400 mL) for 2 days at room temperature. A 10percent sodium acetate solution (3.5 L) was then added dropwise and the white precipitate which formed was filtered and washed with distilled water. Afterward, the residue was stirred in acetone at 50 0C for 30 min after which it was cooled to 00C and filtered. The precipitate was washed with a little acetone and diethyl ether and dried in vacuo. S-Trityl-L-cysteine Ic (205 g, 89percent) was obtained as a white powder. Ic: m.p. 192 °C (decomp) ; 1H NMR (300 MHz, DMSCW5) delta 2.45 (dd, IH, J= 9 Hz, 12 Hz), 2.58 (dd, IH, J= 4.4 Hz, 12 Hz), 2.91 (m, IH), 7.22-7.36 (m, 15H); 13C NMR (75.5 MHz, DMSO- d6): delta 33.8, 53.7, 66.4, 127.1, 127.8, 128.1, 128.4, 129.5, 144.5, 168.4. This material was directly used in the next step without further purification. |
78% | In N,N-dimethyl-formamide; at 20℃; for 48h; | Preparation 75: Synthesis of (R)-3-amino-4-tritylsulfanyl-butyric acid methyl ester hydrochloride; (Step 1); L-cysteine hydrochloride (5Og, 284.7mmol) was dissolved in N,N- dimethylformamide (200ml). Trityl chloride (119g, 427.0mmol) was added thereto, and the mixture was stirred for 48 h at room temperature. After completion of the reaction, 10percent sodium acetate (1.5L) was added. The mixture was filtered to give a solid, which was then added to acetone (1.5L), and stirred for 30 min at 50 °C . The insoluble solid was filtered, and dried to give a trityl compound (80g, Yield 78percent). |
77% | In N,N-dimethyl-formamide; at 20℃; for 48h; | Synthetic Example 1; (R)-3-Mercapto-2-(5-methyl-4-phenyl-thiazoI-2-yIamino)-propionic acid; Step 1 : S-Trityl-L-cysteine falso known as (R)-2-amino-3- (tritylsulfanyl)propanoic acid); L-Cysteine hydrochloride (5.0 g, 31.7 mmol) and trityl chloride (13.5 g, 48.4 mmol) were stirred in DMF (20 ml) for 48 h at room temperature. A 10percent NaOAc solution (175 mL) was then added, and the precipitate was filtered and washed with water. Afterward, the residue was suspended in acetone and stirred at 50 °C for 30 min, then cooled and filtered. The residue was washed with acetone (cold) and diethyl ether. After drying 8.86 g (77percent) S-trityl-L-cysteine was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium acetate; In methanol; water; at 20℃; | (R)-2-(2-Fluoro-phenyl)-thiazolidine-4-carboxylic acid To a solution of L-cysteine hydrochloride (400 mg, 2.54 mmol) in distilled water (4 mL), potassium acetate (274 mg, 2.79 mmol) was added. Once the solids went into solution, methanol (4 mL) was added followed by 2-fluoro-benzaldehyde (325 muL, 3.06 mmol). The reaction was stirred at ambient temperature overnight. The solvent was removed, and no further purification steps were taken. (R)-2-(2-Fluoro-phenyl)-thiazolidine-3,4-dicarboxylic acid 3-benzyl ester |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium acetate; In methanol; water; at 20℃; for 4h; | (R)-2-Oxazol-5-yl-thiazolidine-4-carboxylic acidTo a solution of L-cysteine hydrochloride (446.9 mg, 2.84 mmol) in distilled water (4.3 mL), potassium acetate (319.8 mg, 3.26 mmol) was added. Once the solids went into solution, methanol (4.3 mL) was added followed by <strong>[118994-86-8]oxazole-5-carbaldehyde</strong> (339.0 mg, 3.49 mmol). The reaction was stirred at ambient temperature for 4 hours. The solvent was removed, and no further purification steps were taken. (R)-2-Oxazol-5-yl-thiazolidine-3,4-dicarboxylic acid 3-benzyl ester |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With formaldehyd; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; at -10 - 20℃; | The tert-butoxycarbonyl-N-4-oxo-proline obtained in step S7 and the cysteine hydrochloride were dissolved in a polar proton solvent. Then, carried out reaction again with formaldehyde aqueous solution at -10 ~ 20 C under the action of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride and triethylamine , followed by post-treatment to give (2S) - tert-butyl - 4-oxo-2-(thiazolidine-3-carbonyl)pyrrolidine-1-carboxylate , standby |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | D-Cysteine hydrochloride monohydrate (81.2 mg, 0.462 mmol, 1.1 eq) and 6-amino-cyano- benzothiazole (71 .0 mg, 0.405 mmol, 1 eq) were dissolved in 2:1 MeOH:H20 (1 mL). The resulting solution was allowed to stir at room temperature for 5 mm under a nitrogen atmosphere, after which potassium carbonate (56.5 mg, 0.409 mmol, 1.01 eq) was added. The resulting brightyellow-green solution was allowed to stir for an additional 40 mm, while maintaining an inert atmosphere. Upon consumption of 6-amino-cyanobenzothiazole, as evidenced by TLC analysis, the reaction mixture was diluted with water (4 mL) and washed with EtOAc (1 x 4 mL). The aqueous was then reduced and the resulting precipitate was filtered and washed with cold MeOH (2 x 1 mL). The precipitate was then further purified using reverse phase chromatography elutingwith a gradient of 0-90percent MeOH in water to afford D-aminoluciferin postassium salt as a paleyellow solid (0.123 g, 96percent). [c]ObS: -14° (H20, c = 1). Mp: 111-123°C. 1H-NMR (400 MHz, D20)68.32 (1H, d, J= 8.8 Hz, H-7), 7.79 (1H, s, H-b), 7.55 (1 H, d, J= 8.0 Hz, H-8), 5.72 (1H, m, H-2), 3.8-4.2 (2H, m, H-3). HRMS (ESI+): m/zCalculated for C11H9N302S2K [M+H] 317.9773, found317.9768. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | D-Cysteine hydrochloride monohydrate (30.0 mg, 0.171 mmcl, 1.04 eq) and 2-cyano-6-hydroxy- benzothiazole (29.0 mg, 0.163 mmol, 1 eq) were dissolved in 2:1 MeOH:H20 (1 mL). The resultingsolution was allowed to stir at room temperature for 5 mm under a nitrogen atmosphere, after which potassium carbonate (23.0 mg, 0.164 mmol 1.01 eq) was added. The resulting bright yellow-green solution was allowed to stir for an additional 20 mm, at room temperature, while maintaining the inert atmosphere. Upon consumption of <strong>[939-69-5]2-cyano-6-hydroxybenzothiazole</strong>, as evidenced by TLC analysis, the methanol was removed in vacuo and the remaining aqueoussolution cooled to 0 °C and acidified to pH 3 with 3 M HCI. The aqueous layer was then extracted with EtOAc (5 x 10 mL) and the combined organ ics were dried over Na2SO4, filtered, concentrated in vacuo and purified with column chromatography 3:6:1 DCM:EtOAc:MeOH to provide D-luciferin as a pale yellow solid (39.0 mg, 86 percent). [c]ObS = 290, DMF, c = 1 ([a]1. = -34°, DMF, c = 1). Mp:197-199°C (lit. 196 °C).3 1H-NMR (400 MHz, MeOD) (57.93 (1H, d, J= 8.9 Hz, H-7), 7.35 (iH, d,J= 2.3 Hz, H-b), 7.10 (1H, dd, J= 8.9, 2.3 Hz, H-8), 5.40 (iH, appt, J= 9.0 Hz, H-2), 3.79 (2H, m, H-3) ppm. 13C-NMR (100.6 MHz, CDCI3) oe 172.1 (C-i), 166.2 (C-4), 157.6 (C-9), 157.1 (C-5), 146.8 (C-6), 137.7 (C-il), 124.5 (C-7), 116.8 (C-b), 105.9 (C-8), 78.2 (C-2), 34.5 (C-3) ppm. HAMS (ESI+): m/zCalculated for C11H8N20352 [M+Na] 302.9874, found 302.9868. | |
80% | With potassium carbonate; In methanol; dichloromethane; water; for 0.166667h;Cooling with ice; | <strong>[939-69-5]2-cyano-6-hydroxybenzothiazole</strong> (100 mg, 0.57 mmol) was dissolved in DCM:MeOH = 2:3 (10 mL: 15 mL).And pass N2 to the solution.D-cysteine hydrochloride (136 mg, 0.86 mmol) and K2CO3 (119 mg, 0.86 mmol) were dissolved in DI H2O:MeOH = 1:1 (3 mL).The solution was added dropwise to the above <strong>[939-69-5]2-cyano-6-hydroxybenzothiazole</strong>, and the reaction was carried out in the ice bath for 10 min.After the reaction was completed, DCM and MeOH were distilled off under reduced pressure.The pH was then adjusted to 2-3 with a solution of hydrochloric acid (1M) and a yellow precipitate precipitated.The precipitate was filtered and washed with DI H 2 O until the pH became neutral to give D-luciferin crude product.By column chromatography (silica, DCM: MeOH: AcOH, 10:1:1 v/v/v)Purification gave 128 mg of a pale yellow solid.The yield was 80percent. |
Tags: H-Cys-OH·HCl | L-Cysteine(hydrochloride) | Carboxylic Acids | Organic Building Blocks | 52-89-1
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