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Chemical Structure| 401564-30-5 Chemical Structure| 401564-30-5

Structure of 401564-30-5

Chemical Structure| 401564-30-5

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Product Details of [ 401564-30-5 ]

CAS No. :401564-30-5
Formula : C13H22N2O4S
M.W : 302.39
SMILES Code : O=C(N1[C@H](C(N2CSCC2)=O)C[C@@H](O)C1)OC(C)(C)C
MDL No. :N/A

Safety of [ 401564-30-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of [ 401564-30-5 ]

* 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.

  • Downstream synthetic route of [ 401564-30-5 ]

[ 401564-30-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 401564-30-5 ]
  • [ 401564-36-1 ]
YieldReaction ConditionsOperation in experiment
55% With sulfur trioxide pyridine complex; triethylamine; In dichloromethane; dimethyl sulfoxide; for 2h;Cooling with ice; A mixture of N-tert-butoxycarbonyl-l-trans-hydroxyproline (6a) (69.4 g, 0.3 mol), thiazolidine (29.4 g, 0.33 mmol), HOBT (50.5 g, 0.33 mol) and EDC (63.3 g, 0.33 mol) in DMF (300 mL) was stirred at room temperature for 18 h. The reaction mixture was concentrated under reduced pressure. To the residue was added a saturated aqueous sodium hydrogen carbonate solution and the mixture was extracted with ethyl acetate. The extract was dried and concentrated under reduced pressure to give 3-[(2S,4R)-1-tert-butoxycarbonyl-4-hydroxypyrrolidin-2-ylcarbonyl]thiazolidine (56.3 g, 62%) as a colorless oil. To a solution of the above compound (55.4 g, 183 mmol) and triethylamine (46 mL, 330 mmol) in dichloromethane (350 mL) was added sulfur trioxide-pyridine complex (52.4 g, 329 mmol) in DMSO (150 mL) under ice cooling and the mixture was stirred for 2 h. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with brine, dried and concentrated under reduced pressure. The residue purified by silica gel chromatography with n-hexane/ethyl acetate (1:1, v/v) to give the title compound (30.3 g, 55%) as a white powder. 1H NMR (500 MHz, DMSO-d6): delta 1.36, 1.40 (9H, s), 2.36-2.45 (1H, m), 2.97-3.12 (3H, m), 3.62-3.71 (2H, m), 3.74-3.94 (2H, m), 4.33-4.80 (2H, m), 4.91-5.04 (1H, m).
With sulfur trioxide pyridine complex; triethylamine; In dichloromethane; dimethyl sulfoxide; at 0℃; for 2h; (1) N-tert-Butoxycarbonyl-L-trans-4-hydroxyproline (69.4 g) and thiazolidine (29.4 g) were dissolved in DMF (300 mL), and HOBT (50.5 g) and EDC hydrochloride (63.3 g) were added successively. The mixture was stirred at room temperature for 18 hr. The reaction solution was concentrated and saturated brine and a saturated aqueous sodium hydrogen carbonate solution were added to the concentrate. The mixture was extracted with ethyl acetate. The extract solution was dried and the solvent was evaporated under reduced pressure to give 3-((2S,4R)-1-tert-butoxycarbonyl-4-hydroxy-2-pyrrolizinylcarbonyl)-1,3-thiazolidine (56.3 g) as a colorless transparent oil.(2) The above-mentioned compound (55.4 g) and triethylamine (46 mL) were dissolved in dichloromethane (350 mL), and a solution of pyridine sulfur trioxide complex (52.4 g) in dimethyl sulfoxide (150 mL) was added under ice-cooling and the mixture was stirred for 2 hr. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution. The mixture was extracted with ethyl acetate. The extract solution was washed with saturated brine, dried and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography to give the title compound (30.3 g) as a white solid.1H-NMR(CDCl3)delta 1.47(9H,s), 2.45-2.57(1H,m), 2.70-2.93(1H,m), 2.97-3.22(2H,m), 3.66-3.78(0.6H,m), 3.80-4.10(3H,m), 4.28-4.38(0.4H,m), 4.45-5.08(3H,m).
With sulfur trioxide pyridine complex; triethylamine; In dimethyl sulfoxide; at 0 - 20℃; for 2h; (2S, 4R)-4-Hydroxy-2-(thiazolidine-3-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (3.34 g, 0.0111 mol, Example 17A) was dissolved in DMSO and cooled to 0 C. To the cold solution, triethylamine (7.37 g, 0.0729 mol) and sulfur trioxide pyridine complex (8.44 g, 0.0530 mol) were added. The mixture was stirred at 0 C. for 2 hours, brought to room temperature and quenched with water. The mixture was extracted with ethyl acetate and washed with 1 M HCl (60 mL), saturated NaHCO3 (2*40 mL) and brine (1*30 mL). The organic layer was dried with Na2SO4, filtered, concentrated, and purified by column chromatography (ethyl acetate/hexane, 1/1) to give the titled compound 2.05 g. MS (ESI APCI) m/e 299 (M-H)+; 1H NMR (300 MHz, methanol-d4): delta ppm 5.07 (d, 1H), 4.80 (m, 1H), 4.57-4.68 (m, 2 H), 4.45 (m, 1H), 3.85 (d, 2H), 3.78 (m, 2H), 3.17 (t, 1H), 3.05 (m, 2 H), 2.44-2.49 (d, 1H), 1.47 (s, 9H).
With sulfur trioxide pyridine complex; triethylamine; In dimethyl sulfoxide; at 0℃; for 2h; Example 1A (2S)-4-Oxo-2-(thiazolidine-3-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (2S, 4R)-4-Hydroxy-2-(thiazolidine-3-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (3.34 g, 0.0111 mol, Example 17A) was dissolved in DMSO and cooled to 0 C. To the cold solution, triethylamine (7.37 g, 0.0729 mol) and sulfur trioxide pyridine complex (8.44 g, 0.0530 mol) were added. The mixture was stirred at 0 C. for 2 hours, brought to room temperature and quenched with water. The mixture was extracted with ethyl acetate and washed with 1 M HCl (60 mL), saturated NaHCO3 (2*40 mL) and brine (1*30 mL). The organic layer was dried with Na2SO4, filtered, concentrated, and purified by column chromatography (ethyl acetate/hexane, 1/1) to give the titled compound 2.05g. MS (ESI APCI) m/e 299 (M-H)+; 1H NMR (300 MHz, methanol-d4): delta ppm 5.07 (d, 1H), 4.80 (m, 1H), 4.57-4.68 (m, 2H), 4.45 (m, 1H), 3.85 (d, 2H), 3.78 (m, 2H), 3.17 (t, 1H), 3.05 (m, 2H), 2.44-2.49 (d, 1H), 1.47 (s, 9H).

  • 2
  • [ 401564-30-5 ]
  • [ 144-55-8 ]
  • [ 401564-36-1 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; dimethyl sulfoxide; Reference Example 12 Synthesis of 3-((S)-1-tert-butoxycarbonyl-4-oxo-2-pyrrolidinylcarbonyl)-1,3-thiazolidine The title compound (55.4 g) of Reference Example 9 and triethylamine (46 mL) were dissolved in dichloromethane (350 mL). A solution of sulfur trioxide pyridine complex (52.4 g) in dimethyl sulfoxide (150 mL) was added thereto under ice-cooling, and the mixture was stirred for 2 hr. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, arid the mixture was extracted with ethyl acetate. The extract was washed with brine and dried. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography to give the title compound (30.3 g) as a white solid. 1H-NMR(CDCl3)delta1.47(9H,s), 2.45-2.57(1H,m), 2.70-2.93(1H,m), 2.97-3.22(2H,m), 3.66-3.78(0.6H,m), 3.80-4.10(3H,m), 4.28-4.38(0.4H,m), 4.45-5.08(3H,m).
 

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