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Chemical Structure| 142705-97-3 Chemical Structure| 142705-97-3

Structure of 142705-97-3

Chemical Structure| 142705-97-3

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Product Details of [ 142705-97-3 ]

CAS No. :142705-97-3
Formula : C6H9NO2S
M.W : 159.21
SMILES Code : O=C1NC[C@H](SC(C)=O)C1
MDL No. :MFCD02262101

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Application In Synthesis of [ 142705-97-3 ]

* 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 [ 142705-97-3 ]

[ 142705-97-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 68108-18-9 ]
  • [ 507-09-5 ]
  • [ 142705-97-3 ]
  • 2
  • [ 68108-18-9 ]
  • [ 124-63-0 ]
  • [ 142705-97-3 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; In pyridine; methanol; ethyl acetate; PREPARATION 1 (4R)-4-Acetylthio-2-oxopyrrolidine 1-(1) (4S)-4-Methanesulfonyloxy-2-oxopyrrolidine 1.90 g of <strong>[68108-18-9](4S)-4-hydroxy-2-oxopyrrolidine</strong> were dissolved in 100 ml of pyridine, after which 2.26 g of methanesulfonyl chloride were added dropwise to the solution, whilst stirring and ice-cooling. The resulting mixture was then stirred at room temperature for 1.5 hours, after which the reaction mixture was concentrated by evaporation under reduced pressure. 9 ml of a saturated aqueous solution of sodium hydrogencarbonate were then added to the mixture, and the mixture was again concentrated to dryness by evaporation under reduced pressure. A 1:1 by volume mixture of ethyl acetate and methanol was then added to the resulting residue, after which the insoluble portion was removed by filtration and the soluble portion was concentrated by evaporation under reduced pressure. The residue obtained from the soluble portion was subjected to column chromatography (Merck 9385, 150 ml) through silica gel using a gradient elution method, with mixtures of ethyl acetate and methanol ranging from 9:1 to 4:1 by volume as the eluent. The fractions containing the compound of the invention were combined and concentrated by evaporation under reduced pressure, and the desired compound was recrystallized from a mixture of ethyl acetate and methanol to produce 2.44 g of the title compound as crystals, melting between 137.5 and 139 C. Optical rotation [α]D24 -35.5 (C=1.09, MeOH); Infrared Absorption Spectrum, (KBr) νmax cm-1: 1719, 1697, 1659, 1305, 1177, 1171, 1159, 963.
  • 3
  • [ 68108-18-9 ]
  • [ 507-09-5 ]
  • [ 1972-28-7 ]
  • [ 142705-97-3 ]
YieldReaction ConditionsOperation in experiment
With triphenylphosphine; In tetrahydrofuran; PREPARATION 2 (4R)-4-Acetylthio-2-oxopyrrolidine 380 mg of <strong>[68108-18-9](4S)-4-hydroxy-2-oxopyrrolidine</strong> were suspended in 21 ml of anhydrous tetrahydrofuran, and 1.18 g of triphenylphosphine were added to the suspension at room temperature. 783 mg of diethyl azodicarboxylate were then added dropwise to the solution, whilst maintaining a temperature of -30 C. The mixture was then gradually heated to 4 C., after which the mixture was stirred at the same temperature for 30 minutes to produce a homogeneous mixture. At the end of this time, the reaction mixture was cooled to -20 C., and then 320 μl of thioacetic acid were added dropwise to the cooled mixture. The resulting mixture was gradually heated to a temperature equivalent to ice-cooling; and the mixture was stirred for 1.5 hours at that temperature. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and then subjected to column chromatography (Merck 9385, 60 ml) through silica gel using a gradient elution method, with mixtures of benzene and acetonitrile ranging from 2:1 and 1:1 by volume as the eluent. The desired fraction was concentrated by evaporation under reduced pressure to give 69 mg of a crystalline residue. This residue was recrystallized from a mixture of ethyl acetate and cyclohexane to give 54 mg of the title compound as crystals. The melting point, optical rotation, Infrared Absorption Spectrum and Nuclear Magnetic Resonance Spectrum of the compound obtained in this manner were identical with the corresponding values of the compound obtained in Step (2) of Preparation 1, above.
  • 4
  • [ 68108-18-9 ]
  • [ 142705-97-3 ]
YieldReaction ConditionsOperation in experiment
(1) (4S)-4-Hydroxy-2-pyrrolidone (1.7 g) is treated in the same manner as described in Reference Example 1-(1) to give (4R)-4-acetylthio-2-pyrrolidone (2 g) as an oil. NMR (CDCl3) δppm: 2.29 (1H, dd), 2.35 (3H, s), 2.80 (1H, dd), 3.31 (1H, dd), 3.89 (1H, dd), 4.10-4.23 (1H, m).
 

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