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CAS No. : | 1953-02-2 | MDL No. : | MFCD00004861 |
Formula : | C5H9NO3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YTGJWQPHMWSCST-UHFFFAOYSA-N |
M.W : | 163.19 | Pubchem ID : | 5483 |
Synonyms : |
BRN 1859822;(±)-Tiopronin;Vincol;Epatiol;Capen;Acadione
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.6 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 38.85 |
TPSA : | 105.2 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.39 cm/s |
Log Po/w (iLOGP) : | 0.72 |
Log Po/w (XLOGP3) : | -0.14 |
Log Po/w (WLOGP) : | -0.49 |
Log Po/w (MLOGP) : | -0.54 |
Log Po/w (SILICOS-IT) : | -0.36 |
Consensus Log Po/w : | -0.16 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -0.5 |
Solubility : | 51.7 mg/ml ; 0.317 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.62 |
Solubility : | 3.96 mg/ml ; 0.0243 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.2 |
Solubility : | 104.0 mg/ml ; 0.637 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.85 |
Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P260-P264-P270-P273-P280-P301+P312+P330-P304+P312-P305+P351+P338-P314-P337+P313-P391-P501 | UN#: | 3077 |
Hazard Statements: | H302-H319-H332-H372-H400 | Packing Group: | Ⅲ |
GHS Pictogram: |
* 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 |
---|---|---|
190 g | at 0℃; for 5 h; | 90 g of glycine was added into a multi-necked reaction bottle, and 400 mL of water was added to dissolve the solution, and 64 g of anhydrous sodium carbonate was gradually added. After cooling to 0 ° C, 150 g of 2-mercaptopropionyl chloride was slowly added dropwise,After the addition, a certain amount of sodium carbonate solution was added to keep the reaction solution weakly alkaline. The reaction was continued for 5 hours, acidified to pH 2 with dilute hydrochloric acid, extracted with ethyl acetate and evaporated under reduced pressure to give 190 g of tiopronin |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 135 {2-[2-(4-Sulfamoylphenylcarbamoyl)phenyldisulfanyl]propionylamino}-acetic acid This compound was prepared according to the method of Example 132 using 0.46 g (1.5 mmol) of 4-(3-oxo-3H-benzo[d]isothiazol-2-yl)benzenesulfonamide and 0.25 g (1.5 mmol) of 2-mercapto-propionylglycine. The product was washed with ether and dried in vacuo to give 0.65 g of the title compound, mp 254-256 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
claim 3 wherein the mucolytically active thiol is selected from: N-acetylcysteine; mercaptoethanesulphonic acid; tiopronin; and methylcysteine. | ||
Examples for decomposition by chimeric reducing agents. ... ... 8. 3-Mercapto-4-methyl-1-2,4,-triazole 9. Mercapto-1-propane sulfonic acid, sodium salt 10. N-(2-Mercaptopropionyl) glycine 11. 2-Mercapto pyridine | ||
A non-radioactive thiolate selected from the group consisting of a compound of formula AuSR" and a salt thereof, in which R" is such that a compound of formula HSR" represents a member of the group consisting of: 4,6-dihydroxy-2-mercaptopyrimidine; N-(3-mercaptopropionyl)glycine; and N-(2-mercaptopropionyl)glycine. |
Fifty male rats (Sprague-Dawley, 180-200 g bodyweight) were used for the investigation, subdivided into 5 groups, each consisting of 10 animals, given orally the following compounds (1) 5 percent gum arabic in tap water (2) 5 percent gum arabic in tap water (3) 2-(2-thenoylthio)-propionylglycine--200 mg/kg (4) 2-(2-thenoylthio)-propionylglycine--300 mg/kg (5) 2-mercaptopropionylglycine (300 mg/kg). | ||
Additional preferred compounds include the following: ... NITECAPONE 5-AMINOSALICYLIC ACID PHENYLHYDRAZINE D-PENICILLAMINE TIOPRONIN RESORCINOL QUERCETIN RUTIN ... | ||
Sulphydryl thiol compounds (in particular N-acetylcysteine) Iron chelators (desferioxamine) Anti-inflammatories (e.g., ibuprofen) Phosphocreatine N-2-mercaptopropionyl glycine (MPG) Probucol (and derivatives) Melatonin |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53.3% | In ethanol; water; acetonitrile; | 35A. Formula Ia where A is N-(propionyl)glycine, X is S, and Z is -O-Ethyl A solution of <strong>[1953-02-2]<strong>[1953-02-2]N-(2-mercaptopropionyl)glycin</strong>e</strong> (1.17 g, 7.17 mmol) and ethyl bromopyruvate (1 mL, 7.17 mmol, 90% purity) in acetonitrile (30 mL) was stirred at room temperature for 3 h. After removal of the solvent, the residue was dissolved in a mixed solvent of ethanol (15 mL) and water (15 mL). After the pH was adjusted to 7-8 with satd. NaHCO3 solution, the mixture was stirred at room temperature overnight. The mixture was acidified to pH 1-2 with concentrated hydrochloric acid and then rotary evaporated to dryness. The residue was purified by column chromatography eluted with EtOAc giving 3-[1-(carboxymethylcarbamoyl)ethylsulfanyl]-2-hydroxyacrylic acid ethyl ester as yellow solid (1.06 g, yield 53.3%). 1H NMR (CDCl3, 300.16 MHz) delta (ppm): 9.10 (broad s, 1H), 7.22 (d, J=0.9 Hz, 1H), 4.62 (d, J=17.7 Hz, 1H), 4.53 (d, J=17.7 Hz, 1H), 4.28 (q, J=7.1 Hz, 2H), 3.47 (qd, J=6.2 & 0.9 Hz, 1H), 1.48 (d, J=6.2 Hz, 3H) and 1.30 (t, J=7.1 Hz, 3H). 13C NMR (CDCl3, 75.48 MHz) delta (ppm): 174.02, 165.84, 160.57, 130.27, 120.20, 62.04, 46.76, 37.11, 14.45 and 14.09. MS (ESI) m/z: 260 (M+-OH, 100). |
53.3% | In ethanol; water; acetonitrile; | 35A. Formula Ia where A is N-(Propionyl)glycine, X is S, and Z is -O-Ethyl A solution of <strong>[1953-02-2]<strong>[1953-02-2]N-(2-mercaptopropionyl)glycin</strong>e</strong> (1.17 g, 7.17 mmol) and ethyl bromopyruvate (1 mL, 7.17 mmol, 90% purity) in acetonitrile (30 mL) was stirred at room temperature for 3 h. After removal of the solvent, the residue was dissolved in a mixed solvent of ethanol (15 mL) and water (15 mL). After the pH was adjusted to 7-8 with satd. NaHCO3 solution, the mixture was stirred at room temperature overnight. The mixture was acidified to pH 1-2 with concentrated hydrochloric acid and then rotary evaporated to dryness. The residue was purified by column chromatography eluted with EtOAc giving 3-[1-(carboxymethylcarbamoyl)ethylsulfanyl]-2-hydroxyacrylic acid ethyl ester as yellow solid (1.06 g, yield 53.3%). 1H NMR (CDCl3, 300.16 MHz) delta(ppm): 9.10 (broad s, 1H), 7.22 (d, J=0.9 Hz, 1H), 4.62 (d, J=17.7 Hz, 1H), 4.53 (d, J=17.7 Hz, 1H), 4.28 (q, J=7.1 Hz, 1H), 3.47 (qd, J=6.2 & 0.9 Hz, 1H), 1.48 (d, J=6.2 Hz, 3H) and 1.30 (t, J=7.1 Hz, 3H). 13C NMR (CDCl3, 75.48 MHz) delta(ppm): 174.02, 165.84, 160.57, 130.27, 120.20, 62.04, 46.76, 37.11, 14.45 and 14.09. MS (ESI) m/z: 260 (M+-OH, 100). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; | EXAMPLE 12 Copper bis-N-(2-Mercaptopropionyl)-Glycinate-Cu(C5H8NO3S)2 A solution of 1.8 g of cupric acetate in 50 ml of ethanol was added to a stirred solution of 3.3 g of N-(2-mercaptopropionyl)-glycine in 100 ml of ethanol. The solvent and the formed acetic acid were removed by evaporation in high vacuum (0.01 mm). This yielded 3.8 g of the copper salt of bis-N-(2-Mercaptopropionyl)-glycine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 20℃; for 4h; | <strong>[1953-02-2]<strong>[1953-02-2]N-(2-mercaptopropionyl)glycin</strong>e</strong> (0.02 mol, 3.264 g) was placed in 1,2-dimethoxyethane (50 mL) and dimethylchloroarsine (0.025 mol, 3.52 g) was added dropwise. The reaction mixture was stirred for 4 h at room temperature. A white precipitate of triethylamine hydrochloride salt was then separated by filtration and the solubtion was reduced in volume by evaporation at reduced pressure. The resulting residue was purified by column chromatography to afford the desired product (3.5 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; for 24h; | EXAMPLE 11; N-t2-({6-Ethyl-4-[4-(phenylacetyl)piperazin-1-yl]thieno[2,3-d]pyrimidin-2-yl}thio)propanoyl]glycine EPO <DP n="79"/>The pyrimidine of Example 6 (0.15 g), DMF (3.0 mL), 1 ,8-diazobicyclo[5.4.0]undec-7-ene (0.24 ml_), and N-(2-mercaptopropionyl) glycine (0.183 g) were placed in a 2 dram screw cap vial and placed in a Lab-Line MAX Q2000 orbital shaker for 24 hours. The mixture was partitioned between 1 N HCI and ethyl acetate. The layers were separated and the organic layer washed three times with 1N HCI, dried over anhydrous magnesium sulfate and concentrated to dryness. The residue was chromatographed on silica gel (100 mL) using 12% methanol in dichloromethane with 0.2% glacial acetic acid to give 0.0394 g (20%) of the title compound: MS (ESI+) for C25 H29 N5 O4 S2 m/z 528Lambda4 (M+H)+; 1H NMR (CDCI3) delta 1.34 (t, 3 H), 1.57 (d, 2 H), 2.83 (q, 2 H), 3.62 (m, 2 H), 3.72 (m, 2 H), 3.74-3.84 (m, 6 H), 3.9-4.1 (m, 2 H), 4.4 (m, 1 H), 6.85 (s, 1 H), 7.26 (m, 3 H), 7.31 (m, 2 H), 7.85 (m, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; for 24h; | EXAMPLE 30; N-[2-({4-[4-(1 ,1 '-Biphenyl-4-ylcarbonyl)piperazin-1 -yl]-6-ethylthieno[2,3-d]pyrimidin-2- yl}thio)propanoyl]glycineThe pyrimidine of Example 21 (0.15 g), DMF (2.5 ml_), 1 ,8-diazobicyclo[5.4.0]undec-7-ene (0.22 ml_), and N-mercaptopropionyl glycine (0.159 mL) were placed in a 2 dram screw cap vial and placed in a Lab-Line MAX Q2000 orbital shaker for 24 hours. Added an additional (0.159 g) N- mercaptopropionyl glycine and 1,8-diazobicyclo[5.4.0]undec-7-ene (0.22 mL) and continued to shake for an additional 24 hours. The mixture was partitioned between 1N HCI and ethyl acetate. The layers were separated and the organic layer washed four times with 1N HCI, dried over anhydrous magnesium sulfate and concentrated to dryness to give 0.0956g (43%) of the title compound: 1H NMR (CDCI3) delta 1.32 (t, 3 H), 4.55 (m, 4 H), 2.88 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | IR and NMR spectra in agreement. According to a similar process, equimolar amounts (289 mM) of N-(2-mercapto-propionyl)-glycine and of 3-(chloroacetyl)-thiazolidine, were reacted, yielding 43.8 g (52% yield) of 2-[2-[(3-thiazolidyl)carbonylmethylthio]-propionamide]acetic acid (9) (m.p.=122-126 C.). Elemental analysis: (for C10 H16 N2 O4 S2; MW=292.37). Calc. %: C, 41.08; H, 5.51; N, 9.58. Found %: C, 41.00; H, 5.25; N, 9.33. | |
52% | According to a similar process, equimolar amounts (289 mM) of N-(2-mercapto-propionyl)-glycine and of 3-(chloroacetyl)-thiazolidine, were reacted, yielding 43.8 g (52% yield) of 2-[2-[(3-thiazolidyl)carbonylmethylthio]-propionamide]acetic acid (9) (m.p. = 122-126C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; water; trifluoroacetic acid; | EXAMPLE 6 S-(2-phenylcarbamoyl-phenylselenyl)-DL-2-mercaptopropionylglycine 1 g (3,65 mmol) of 2-phenyl-1,2-benzisoselenazole-3(2H)-one and 0,6 g (3,68 mmol) of DL-2-mercaptopropionylglycine are dissolved in 15 ml trifluoroacetic acid and the stirring is continued for 18 hours at room temperature. Then, 100 ml of an ice/water mixture is added to the solution. The obtained precipitate is extracted with dichloromethane. After drying the solvent and evaporating in vacuum, the solid is then recristallized from ethanol/water (7:3). Yield: 1,5 g (94% of the theory), m.p. 199 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 15 S-(2-phenylcarbamoyl-6-methoxy-phenylselenyl)-DL-2-mercaptopropionylglycine Prepared similar to example 1 from 3,0 g (9,87 mmol) of 7-methoxy-2-phenyl-1,2-benzisoselenazole-3(2H)-one and 1,63 g (10 mmol) of DL-2-mercaptopropionylglycine. Yield: 4,5 g (97,6% of the theory), m.p. 242-245 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | In dichloromethane; triethylamine; | EXAMPLE IX 6-Methyl[1,4]thiazine-2,5-dione A solution of N-(2-mercaptopropanoyl) glycine (5 g, 0.031 mole) in methylene chloride (250 ml) was chilled in an ice bath and triethylamine (3.1 g, 0.031 mole) was added. Ethyl chloroformate (3.4 g, 0.031 mole) in methylene chloride (25 ml) was added dropwise over 15 minutes. The resulting solution was then stirred for two and a half hours at room temperature. The methylene chloride was washed with water, saturated aqueous sodium chloride, and dried over magnesium sulfate. Filtration and evaporation of the solvent afforded the crude product as a yellow oil which was chromatographed on silica-gel (CHCl3) to yield colorless crystals of 6-methyl[1,4]thiazine-2,5-dione (1.5 g, 30%) after crystallization from ether-hexane, m.p. 81-83. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50.2% | With hydrogenchloride; In water; | EXAMPLE 7 N-[2-(S-acetamidomethyl)mercaptopropionyl]glycine 2-mercaptopropionylglycine, 20.0 g (122.6 mmoles), and N-hydroxymethyl-acetamide, 12.0 g (134.8 mmoles), are dissolved in 200 ml of deionized water. The solution is cooled on an ice bath and 100 ml of conc. HCl is added in one portion. The mixture is stirred on ice for one hour and at room temperature overnight. A white precipitate begins to form within 1-2 hours. The reaction mixture is cooled on ice for 4 hours. The white precipitate is filtered, washed with a few mls of ice-cold water, then 2*200 ml Et2 O. The product is dried by air suction for one hour and uncer vacuum overnight to yield 14.4 g (50.2% yield) of the white, crystalline product N-[2-(S-acetamidomethyl)mercaptopropionyl]glycine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.4% | In water; | EXAMPLE 8 N-[2-(S-benzamidomethyl)mercaptopropionyl]glycine 2-mercaptopropionylglycine, 5.0 g (30.6 mmoles), and N-hydroxymethyl-benzamide, 5.0 g (33.1 mmoles), are dissolved in 100 ml of deionized water. The solution is cooled on an ice bath and 50 ml of conc. aqueous HCl is added in one portion. The mixture is stirred on ice for one hour and at room temperature overnight. A white precipitate begins to form within thirty minutes. After this period the reaction mixture is cooled on ice for 4 hours. The white precipitate is filtered, washed with ice-cold water, then 2*200 ml Et2 O. The product is dried by air suction for an hour and under vacuum overnight to yield 8.4 g (94.4% yield) of the white, crystalline product N-[2-(S-benzamidomethyl)mercaptopropionyl]glycine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In trifluoroacetic acid; | (b) To a solution of alpha-mercaptopropionyl glycine (50 g; 0.307 moles) in 300 ml of trifluoroacetic acid, were added 79.9 g (0.307 moles) of triphenylcarbinol. The thus obtained solution was kept under stirring at room temperature for 15 minutes. The excess of trifluoroacetic acid was removed by evaporation and the residue taken up with ether. Filtration yielded a white solid, which was then washed with ether and dried in vacuo to constant weight. M.P. 179-180 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With nitrogen; In ethanol; | STEP A: ethyl 2-mercapto propionylglycinate Nitrogen was bubbled through a suspension of 50 g of 2-mercapto propionylglycinate in 100 ml of absolute ethanol for 30 minutes and then gaseous hydrogen chloride was bubbled therethrough with stirring for one hour. The mixture stood overnight under a hydrogen chloride atmosphere and then the ethanol was evaporated. The residual oil was dissolved in 150 ml of ether and the ether solution was washed with water, dried over magnesium sulfate and evaporated to dryness to obtain 52 g of ethyl 2-mercapto propionylglycinate in the form of a colorless oil which was used as is for the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,2-dimethoxyethane; | Example 8 Preparation of N-(2-S-dimethylarsinothiopropionyl)glycine <strong>[1953-02-2]<strong>[1953-02-2]N-(2-mercaptopropionyl)glycin</strong>e</strong> (0.02 mol, 3.264 g) was placed in 1,2-dimethoxyethane (50 mL) and dimethylchloroarsine (0.025 mol, 3.52 g) was added dropwise. The reaction mixture was stirred for 4 h at room temperature. A white precipitate of triethylamine hydrochloride salt was then separated by filtration and the solubtion was reduced in volume by evaporation at reduced pressure. The resulting residue was purified by column chromatography to afford the desired product (3.5 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | Step 2: (R)-2-Acetamido-3-((2',4'-difluoro-3-(methoxycarbonyl)biphenyl-4-yloxy) carbonylthio)propanoic acid (Method A) 4-Nitrophenyl chloroformate (300 mg, 1.488 mmol) was added to a solution of methyl 2',4'- difluoro-4-hydroxybiphenyl-3-carboxylate (600 mg, 2.27 mmol) and Et3N (0.5 mL, 3.587 mmol) in CH2CI2 (20 mL). The reaction mixture was refiuxed for 4 h and allowed to reach r.t. It was diluted with CH2CI2 (70 mL) and washed with NaHC03 (saturated aqueous solution, 100 mL). The organic layer was dried over Na2S04 (anhydrous), filtered and concentrated. The crude residue was submitted to next step without further purification. The crude residue from previous step was dissolved in DMF (16 mL) and NAC (360 mg, 2.20 mmol) was added. The reaction mixture was stirred at r.t. for 15 min and Et3N (1.0 mL, 7.1 1 mmol) was added. The reaction was stirred at r.t. overnight (16 h). It was poured into I LO (50 mL), taken up to pH ------ 3 by adding HC1 (5% aqueous solution) and it was extracted with CH2CI2 (2x40 mL). The organic layer was dried over Na2S04 (anhydrous), filtered and concentrated (DMF was concentrated o f at high vacuum pump). The crude residue was flash chromatographed on SiC)2 (25% MeOH/CFLCL;) to furnish a solid that was slurred with Et20 (6 mL), to furnish 88 mg of (R)-2-acetamido-3-((2',4'-difluoro-3-(methoxycarbonyl)biphenyl- 4-yloxy)carbonyl thio)propanoie acid (off-white solid, yield: 13%).; Exam le B- 18 2-(2-((2',4'-DifluoiO-3-(methoxycarbonyl)biphenyl-4-yloxy)carbonylthio) propanamido)acetic acid The compound was synthesized from methyl 2',4 FontWeight="Bold" FontSize="10" -difluoro-4-hydroxybiphenyl-3-carboxylate and A'-( 2-nicrcaptopropionyl)glycine following the experimental procedure detailed in Method A, avoiding the addition of Et3N to the reaction medium. The crude residue was purified by flash chromatography on Si02 (2- 10% MeOH/CH2Cl2) to give a colourless oil that was precipitated by stirring at -78 C in the presence of hexanes, to furnish 2-(2-((2'.4'- difluoro-3-(methoxycarbonyl)biphenyl-4-yloxy)carbonylthio)propanamido)acetic acid (white solid, yield: 19%). NMR (CD3OD, 250 MHz) delta ppm: 8.1 1 (s, 1 11 ), 7.78 (d, J = 8.5 Hz, 1H), 7.55 (m, 1H), 7.34 (d, J = 7.34 Hz, 1H), 7.05-7.14 (m, 211). 4.24 (c, J = 6.6 Hz, 1H), 3.85-3.99 (m, 5H), 1.61 (d, J = 6.6 Hz, 3H). EI MS: m/z = 454 (M+l ). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: To a 50 mM HEPES solution (pH 5.0, 7.0 or 8.5) of pPyNFP (final concentration is 7.5M), 100× concentrated amino acid or biothiol (final concentration is 0.75-750muM) in ultrapure water was added and then stirred at 24C. For isolation of the reaction product between pPyNFP-d20 and cysteine, the reaction mixture was purified by HPLC with CosmoSil 5C18-AR-II (10.0×250mm) using a mixed solvent CH3CN/H2O containing 0.1% trifluoroacetic acid (TFA). Flow rate was 3.0mL/min. Gradient conditions for CH3CN in 0.1% aqueous TFA were 0-40% in 60min. For detection of NFP and NCP moieties, the absorptions at 550nm were employed. After the HPLC separation, the major fraction whose retention time was 41min was collected and lyophilized. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | To a solution of carboxyl group-containing thiol compound 2o (0.263 mmol) in THF (5 mL) were added triethylamine (0.789 mmol) and bromo-N-methylmaleimide 1a (0.263 mmol). The solution was stirred at room temperature for specified time before NaHSO4 (2.63 mmol) and anhydrous MgSO4 (1 g) was added successively. The mixture was stirred vigorously for 1 hour at room temperature. After the carboxylic acid was entirely released from thetriethylamine salt, the resulting mixture was vacuo-filtered. The residue was washed with THF for several times. The combined filtrate was evaporated and purified by a flash column chromatography (dichloromethane/methanol,10/1, v/v) to provide thiol-protected compound 3o aswhite solid in 92% yield. 1H NMR (400MHz, DMSO-d6): delta 12.69(bs, 1H), 8.66 (t, J = 5.6Hz, 1H), 6.57 (s, 1H), 4.18 (q, J =6.8 Hz, 1H), 3.80 (t, J =5.2 Hz, 2H), 2.86 (s, 3H), 1.50 (d, J = 7.2 Hz, 3H); 13C NMR (100 MHz, DMSO-d6): delta 171.4, 170.5, 170.0, 168.4, 148.5, 119.9, 44.0,41.4, 24.2, 18.1; HRMS (EI) m/z calcd for C10H12N2O5S (M+H)273.0545, found 273.0544. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
190 g | With sodium carbonate; at 0℃; for 5h; | 90 g of glycine was added into a multi-necked reaction bottle, and 400 mL of water was added to dissolve the solution, and 64 g of anhydrous sodium carbonate was gradually added. After cooling to 0 C, 150 g of 2-mercaptopropionyl chloride was slowly added dropwise,After the addition, a certain amount of sodium carbonate solution was added to keep the reaction solution weakly alkaline. The reaction was continued for 5 hours, acidified to pH 2 with dilute hydrochloric acid, extracted with ethyl acetate and evaporated under reduced pressure to give 190 g of tiopronin |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47 g | With edetate disodium; In methanol; at 60℃; under 2250.23 Torr; for 5h;Autoclave; Inert atmosphere; | 28 g (0.20 mol) of zinc chloride and 30 mL of aqueous ammonia were weighed into a high pressure autoclave,Add analytical pure A 150mL,Stirring to dissolve,(0.20 mol / l) was added, 130 mL of methanol of analytical grade and 0.5 g of disodium ethylenediaminetetraacetate were added to the autoclave. Nitrogen gas was introduced into the autoclave to bring the pressure to 0.3 MPa,The reaction was carried out at 60 C for 5 h. The insoluble matter was removed by filtration and filtration. The filtrate was placed in an ultrasonic reactor. The precipitating agent was added to 100 mL of acetone at 0 C. The precipitate was coagulated by ultrafiltration at 80 KHz. 60 C drying, tiopronin zinc 47g, yield 90%, chloride ion detection products that chloride-free existence. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 20℃; | A mixture of tiopronin (0.10 g, 1.0 eq), (2,5-dioxopyrrolidin-1-yl)oxycarbonyloxymethyl acetate (1.0 eq), and NaHCO3 (or TEA) (2.0 eq) in ACN/water (or DMF) (5 mL) was stirred at 20 C. overnight. The reaction was concentrated in vacuo to a residue and then purified by reverse-phase (C-18) liquid chromatography using water and acetonitrile as eluents to yield compound (1). MS (ESI): m/z 280.0 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In methanol; water; at 20℃; for 4h; | As shown in Figure 2,303 mg of CpFe(CO)2I was added to 30 mL of methanol (CH3OH), and 326.38 mg of tiopronin and 250 muL of triethylamine (NEt3) were added to 2 mL of deionized water.The aqueous solution is added dropwise to the methanol solution,React at room temperature for 4 h,Get a red solution,The solvent (methanol and deionized water) is removed by rotary evaporation.Then use a silica gel column for separation.The eluent was ethyl acetate:methanol = 1:1.Finally, a pure red oily substance is obtained.Temporarily named as compound Fe2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.5% | a. Add 28kg of purified water, 8kg of sodium sulfide and 3kg of sublimation sulfur to the reaction kettle, heat to 65C and stir until completely dissolved, to obtain a sodium disulfide solution, drop to normal temperature, and set aside;b. Add 25Kg of purified water to the reaction kettle, control the temperature in the kettle not to exceed 80 and add 26kg of sulfuric acid dropwise.c. Add 15Kg of <strong>[85038-45-5]2-chloropropionylglycine</strong> and 5.5Kg of sodium carbonate to the reaction kettle, start stirring, slowly add 60Kg of purified water, and stir until completely dissolved; then add the sodium disulfide solution prepared in step a, Stir for 3 minutes, then heat to 45 for 8 hours;d. Reduce the temperature to 5C, dropwise add the sulfuric acid solution prepared in step b, and stir for 5 minutes; then add 12Kg of zinc powder and stir for 3 minutes. After the addition, heat up to 20C for 1 hour, then add 1.5kg of activated carbon to decolorize; Then filtered, the filtrate was extracted with ethyl acetate 3 times, each time the amount of ethyl acetate was 120Kg; then the ester layer was collected;e. Concentrate the ester layer at a temperature not exceeding 60C under reduced pressure and concentrate until crystals are precipitated. After the concentration is completed, add ethyl acetate 20Kg while stirring and discharge to the crystallization barrel. Cool to 0C and crystallize; Then wash with 5Kg cold ethyl acetate, then spin dry, put the spin-dried material into the tray; depressurize to -0.02Mpa, control the temperature and dry in vacuum at 45 for 4 hours, that is, Tiopronin; yield: 76.5% , Purity: 99.88%. |
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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