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[ CAS No. 339-72-0 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 339-72-0
Chemical Structure| 339-72-0
Structure of 339-72-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 339-72-0 ]

CAS No. :339-72-0 MDL No. :MFCD00064324
Formula : C3H6N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 102.09 Pubchem ID :-
Synonyms :
(S)-Cycloserine;(S)-4-Amino-3-isoxazolidone;BRN 0080799;L-Oxamicina;Cyclo-L-serine;L-4-amino 3-Isoxazolidinone;(-)-Cycloserine;Levcycloserinum;Levcicloserina;Levcycloserine

Calculated chemistry of [ 339-72-0 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.67
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 25.13
TPSA : 64.35 Ų

Pharmacokinetics

GI absorption : Low
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) : -7.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.52
Log Po/w (XLOGP3) : -1.51
Log Po/w (WLOGP) : -2.01
Log Po/w (MLOGP) : -1.68
Log Po/w (SILICOS-IT) : -0.44
Consensus Log Po/w : -1.02

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.48
Solubility : 307.0 mg/ml ; 3.01 mol/l
Class : Highly soluble
Log S (Ali) : 0.66
Solubility : 471.0 mg/ml ; 4.62 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.27
Solubility : 192.0 mg/ml ; 1.88 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.73

Safety of [ 339-72-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 339-72-0 ]

* 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 [ 339-72-0 ]

[ 339-72-0 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 163682-35-7 ]
  • [ 339-72-0 ]
YieldReaction ConditionsOperation in experiment
With ion exchanger
  • 2
  • [ 103758-42-5 ]
  • [ 339-72-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogen bromide; palladium Hydrogenation.folgendes Behandeln mit NH3;
  • 3
  • [ 103-80-0 ]
  • [ 339-72-0 ]
  • [ 66444-64-2 ]
  • 4
  • [ 339-72-0 ]
  • [ 115059-34-2 ]
YieldReaction ConditionsOperation in experiment
With sulfur trioxide; lithium diisopropyl amide 1.) THF, -78 deg C, 2.) DMF, 0 deg C,; Multistep reaction;
  • 5
  • [ 82911-69-1 ]
  • [ 339-72-0 ]
  • [ 219829-15-9 ]
YieldReaction ConditionsOperation in experiment
With N,O-bis-(trimethylsilyl)-acetamide 1.) CD2Cl2, 45 min, 2.) overnight; Yield given. Multistep reaction;
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium hydroxide; hydroxylamine
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate
YieldReaction ConditionsOperation in experiment
With D-tartaric acid
With D-tartaric acid
  • 9
  • [ 24424-99-5 ]
  • [ 339-72-0 ]
  • [ 118236-32-1 ]
YieldReaction ConditionsOperation in experiment
41% With triethylamine In tetrahydrofuran; water at 0 - 20℃; 73.1 Stepl : Compound 73a (500mg, 4.9mmol) and TEA (990mg, 9.8mmol) were dissolved in a mixture of THF/water (75mL, WV 2:1). (Boc)2O (1.18g, 5.4mmol) was added drop-wise under ice cooling. After the addition was complete, the mixture was warmed to room temperature and stirred overnight. The mixture was evaporated to dryness and the residue was purified by column chromatography (EA:PE=1 :3) to provide compound 73b (406mg, 41%) as white solid.
  • 10
  • [ 773103-94-9 ]
  • [ 339-72-0 ]
  • 3-[5-bromo-4-(2,4-difluoro-benzyloxy)-2-methyl-6-oxo-6H-pyrimidin-1-yl]-4-methyl-N-((S)-3-oxo-isoxazolidin-4-yl)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 48h; 14 3-[5-Bromo-4-(2,4-difluoro-benzyloxy)-2-methyl-6-oxo-6H-pyrimidin-1-yl]-4- methyl-benzoic acid (36 mg, 0.078 mmol), L-cycloserine (16 mg, 0.16 mmol), HATU (32 mg, 0.084 mmol), DIEA (18 μl, 0.086 mmol) were dissolved in DMF (4 ml). It was stirred for 48 h at rt, concentrated, purified by prep. HPLC and lyophilized to yield the title compound as a white, fluffy solid. Physical Data: 1H-NMR (400 MHz1 d6-DMSO) δ 11.57 (br s, 1 H), 9.00 (br s, 1H), 7.93 (d, J = 8.0 Hz, 1H), 7.83 (dd, J = 1.6, 4.0 Hz, 1H), 7.67 (q, J = 7.9 Hz, 1H), 7.58 (d, J = 8.0 Hz, 1 H), 7.34 (dt, J = 2.1, 9.8 Hz, 1H), 7.17 (dt, J = 2.4, 8.4 Hz, 1 H)1 5.56 (d, J = 12.0 Hz, 1H), 5.48 (d, J = 12.4 Hz, 1H), 5.08-4.98 (m, 1H), 4.58 (dt, 1H), 4.08 (q, J = 9.1 Hz, 1 H), 2.12, 2.11 (2 s, 3H), 2.08 (s, 3H); MS (m/z): 549, 551 [M+1]+.
  • 11
  • [ 98-09-9 ]
  • [ 339-72-0 ]
  • [ 1248593-34-1 ]
YieldReaction ConditionsOperation in experiment
17% With sodium hydrogencarbonate; sodium carbonate at 0 - 4℃; buffer; Inert atmosphere;
  • 12
  • [ 109-65-9 ]
  • [ 339-72-0 ]
  • C7H14N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: L-cycloserine With Et4N(1+)CH2CN(1-) In N,N-dimethyl-formamide; acetonitrile at 20℃; for 0.25h; Inert atmosphere; Methyl cellulose gel; Stage #2: 1-bromo-butane In N,N-dimethyl-formamide; acetonitrile at 20℃; for 2h; Inert atmosphere; Methyl cellulose gel; General remarks and procedure General procedure: Constant current electrolyses (I = 25 mA cm-2) were performed under a nitrogen atmosphere, at 20°C, using an Amel Model 552 potentiostat equipped with an AmelModel 731 integrator. All the experiments were carried out in a divided glass cell separated through a porous glass plug filled up with a layer of gel (i.e., methylcellulose 0.5% vol dissolved in DMF-Et4NPF6 1.0 mol dm-3); Pt spirals (apparent areas 0.8 cm2) were used both as cathode and anode. MeCN-Et4NPF6 0.1 mol dm-3 was used as solvent-supporting electrolyte system (catholite: 20 cm3; anolite: 5 cm3).1 mmol of substrate was present in the catholyte (except for D-cycloserine, which was added to the catholyte after the end of the electrolysis). After 145 C (if not otherwise stated) were passed, the current was switched off and 1 mmol of alkylating agent was added to the catholyte. The solution was kept under stirring at room temperature for 2 hours, than the solvent was evaporated under reduced pressure and the residue was extracted three times with diethyl ether. The products were purified by flash column chromatography, using a mixture of ethyl acetate/light petroleum ether 2/8 in volume. The reactions on D-cycloserine were carried out following the general method, but the substrate was added to the catholyte after the end of the electrolysis. After 15 minutes at room temperature, the alkylating agent was added and the solution was kept under stirring at rt for 2 hours. The solvent was evaporated under reduced pressure and the residue was treated with 1 cm3 of saturated acqueous NaHCO3 and 1 mmol of ethyl chloroformate, at 0°C, for 2 h. The solution was then acidified with diluted HCl (pH 4) and extracted with diethyl ether. The products were purified by flash column chromatography.
  • 13
  • [ 111-83-1 ]
  • [ 339-72-0 ]
  • C11H22N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: L-cycloserine With Et4N(1+)CH2CN(1-) In N,N-dimethyl-formamide; acetonitrile at 20℃; for 0.25h; Inert atmosphere; Methyl cellulose gel; Stage #2: 1-bromo-octane In N,N-dimethyl-formamide; acetonitrile at 20℃; for 2h; Inert atmosphere; Methyl cellulose gel; General remarks and procedure General procedure: Constant current electrolyses (I = 25 mA cm-2) were performed under a nitrogen atmosphere, at 20°C, using an Amel Model 552 potentiostat equipped with an AmelModel 731 integrator. All the experiments were carried out in a divided glass cell separated through a porous glass plug filled up with a layer of gel (i.e., methylcellulose 0.5% vol dissolved in DMF-Et4NPF6 1.0 mol dm-3); Pt spirals (apparent areas 0.8 cm2) were used both as cathode and anode. MeCN-Et4NPF6 0.1 mol dm-3 was used as solvent-supporting electrolyte system (catholite: 20 cm3; anolite: 5 cm3).1 mmol of substrate was present in the catholyte (except for D-cycloserine, which was added to the catholyte after the end of the electrolysis). After 145 C (if not otherwise stated) were passed, the current was switched off and 1 mmol of alkylating agent was added to the catholyte. The solution was kept under stirring at room temperature for 2 hours, than the solvent was evaporated under reduced pressure and the residue was extracted three times with diethyl ether. The products were purified by flash column chromatography, using a mixture of ethyl acetate/light petroleum ether 2/8 in volume. The reactions on D-cycloserine were carried out following the general method, but the substrate was added to the catholyte after the end of the electrolysis. After 15 minutes at room temperature, the alkylating agent was added and the solution was kept under stirring at rt for 2 hours. The solvent was evaporated under reduced pressure and the residue was treated with 1 cm3 of saturated acqueous NaHCO3 and 1 mmol of ethyl chloroformate, at 0°C, for 2 h. The solution was then acidified with diluted HCl (pH 4) and extracted with diethyl ether. The products were purified by flash column chromatography.
  • 14
  • [ 2969-81-5 ]
  • [ 339-72-0 ]
  • C9H16N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: L-cycloserine With Et4N(1+)CH2CN(1-) In N,N-dimethyl-formamide; acetonitrile at 20℃; for 0.25h; Inert atmosphere; Methyl cellulose gel; Stage #2: Ethyl 4-bromobutyrate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 2h; Inert atmosphere; Methyl cellulose gel; General remarks and procedure General procedure: Constant current electrolyses (I = 25 mA cm-2) were performed under a nitrogen atmosphere, at 20°C, using an Amel Model 552 potentiostat equipped with an AmelModel 731 integrator. All the experiments were carried out in a divided glass cell separated through a porous glass plug filled up with a layer of gel (i.e., methylcellulose 0.5% vol dissolved in DMF-Et4NPF6 1.0 mol dm-3); Pt spirals (apparent areas 0.8 cm2) were used both as cathode and anode. MeCN-Et4NPF6 0.1 mol dm-3 was used as solvent-supporting electrolyte system (catholite: 20 cm3; anolite: 5 cm3).1 mmol of substrate was present in the catholyte (except for D-cycloserine, which was added to the catholyte after the end of the electrolysis). After 145 C (if not otherwise stated) were passed, the current was switched off and 1 mmol of alkylating agent was added to the catholyte. The solution was kept under stirring at room temperature for 2 hours, than the solvent was evaporated under reduced pressure and the residue was extracted three times with diethyl ether. The products were purified by flash column chromatography, using a mixture of ethyl acetate/light petroleum ether 2/8 in volume. The reactions on D-cycloserine were carried out following the general method, but the substrate was added to the catholyte after the end of the electrolysis. After 15 minutes at room temperature, the alkylating agent was added and the solution was kept under stirring at rt for 2 hours. The solvent was evaporated under reduced pressure and the residue was treated with 1 cm3 of saturated acqueous NaHCO3 and 1 mmol of ethyl chloroformate, at 0°C, for 2 h. The solution was then acidified with diluted HCl (pH 4) and extracted with diethyl ether. The products were purified by flash column chromatography.
  • 15
  • [ 459-46-1 ]
  • [ 339-72-0 ]
  • C10H11FN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: L-cycloserine With Et4N(1+)CH2CN(1-) In N,N-dimethyl-formamide; acetonitrile at 20℃; for 0.25h; Inert atmosphere; Methyl cellulose gel; Stage #2: 4-Fluorobenzyl bromide In N,N-dimethyl-formamide; acetonitrile at 20℃; for 2h; Inert atmosphere; Methyl cellulose gel; General remarks and procedure General procedure: Constant current electrolyses (I = 25 mA cm-2) were performed under a nitrogen atmosphere, at 20°C, using an Amel Model 552 potentiostat equipped with an AmelModel 731 integrator. All the experiments were carried out in a divided glass cell separated through a porous glass plug filled up with a layer of gel (i.e., methylcellulose 0.5% vol dissolved in DMF-Et4NPF6 1.0 mol dm-3); Pt spirals (apparent areas 0.8 cm2) were used both as cathode and anode. MeCN-Et4NPF6 0.1 mol dm-3 was used as solvent-supporting electrolyte system (catholite: 20 cm3; anolite: 5 cm3).1 mmol of substrate was present in the catholyte (except for D-cycloserine, which was added to the catholyte after the end of the electrolysis). After 145 C (if not otherwise stated) were passed, the current was switched off and 1 mmol of alkylating agent was added to the catholyte. The solution was kept under stirring at room temperature for 2 hours, than the solvent was evaporated under reduced pressure and the residue was extracted three times with diethyl ether. The products were purified by flash column chromatography, using a mixture of ethyl acetate/light petroleum ether 2/8 in volume. The reactions on D-cycloserine were carried out following the general method, but the substrate was added to the catholyte after the end of the electrolysis. After 15 minutes at room temperature, the alkylating agent was added and the solution was kept under stirring at rt for 2 hours. The solvent was evaporated under reduced pressure and the residue was treated with 1 cm3 of saturated acqueous NaHCO3 and 1 mmol of ethyl chloroformate, at 0°C, for 2 h. The solution was then acidified with diluted HCl (pH 4) and extracted with diethyl ether. The products were purified by flash column chromatography.
  • 16
  • [ 20443-98-5 ]
  • [ 339-72-0 ]
  • C10H10Cl2N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: L-cycloserine With Et4N(1+)CH2CN(1-) In N,N-dimethyl-formamide; acetonitrile at 20℃; for 0.25h; Inert atmosphere; Methyl cellulose gel; Stage #2: 2,6-Dichlorobenzyl bromide In N,N-dimethyl-formamide; acetonitrile at 20℃; for 2h; Inert atmosphere; Methyl cellulose gel; General remarks and procedure General procedure: Constant current electrolyses (I = 25 mA cm-2) were performed under a nitrogen atmosphere, at 20°C, using an Amel Model 552 potentiostat equipped with an AmelModel 731 integrator. All the experiments were carried out in a divided glass cell separated through a porous glass plug filled up with a layer of gel (i.e., methylcellulose 0.5% vol dissolved in DMF-Et4NPF6 1.0 mol dm-3); Pt spirals (apparent areas 0.8 cm2) were used both as cathode and anode. MeCN-Et4NPF6 0.1 mol dm-3 was used as solvent-supporting electrolyte system (catholite: 20 cm3; anolite: 5 cm3).1 mmol of substrate was present in the catholyte (except for D-cycloserine, which was added to the catholyte after the end of the electrolysis). After 145 C (if not otherwise stated) were passed, the current was switched off and 1 mmol of alkylating agent was added to the catholyte. The solution was kept under stirring at room temperature for 2 hours, than the solvent was evaporated under reduced pressure and the residue was extracted three times with diethyl ether. The products were purified by flash column chromatography, using a mixture of ethyl acetate/light petroleum ether 2/8 in volume. The reactions on D-cycloserine were carried out following the general method, but the substrate was added to the catholyte after the end of the electrolysis. After 15 minutes at room temperature, the alkylating agent was added and the solution was kept under stirring at rt for 2 hours. The solvent was evaporated under reduced pressure and the residue was treated with 1 cm3 of saturated acqueous NaHCO3 and 1 mmol of ethyl chloroformate, at 0°C, for 2 h. The solution was then acidified with diluted HCl (pH 4) and extracted with diethyl ether. The products were purified by flash column chromatography.
  • 17
  • [ 402-49-3 ]
  • [ 339-72-0 ]
  • C11H11F3N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: L-cycloserine With Et4N(1+)CH2CN(1-) In N,N-dimethyl-formamide; acetonitrile at 20℃; for 0.25h; Inert atmosphere; Methyl cellulose gel; Stage #2: 4-bromomethyltrifluoromethylbenzene In N,N-dimethyl-formamide; acetonitrile at 20℃; for 2h; Inert atmosphere; Methyl cellulose gel; General remarks and procedure General procedure: Constant current electrolyses (I = 25 mA cm-2) were performed under a nitrogen atmosphere, at 20°C, using an Amel Model 552 potentiostat equipped with an AmelModel 731 integrator. All the experiments were carried out in a divided glass cell separated through a porous glass plug filled up with a layer of gel (i.e., methylcellulose 0.5% vol dissolved in DMF-Et4NPF6 1.0 mol dm-3); Pt spirals (apparent areas 0.8 cm2) were used both as cathode and anode. MeCN-Et4NPF6 0.1 mol dm-3 was used as solvent-supporting electrolyte system (catholite: 20 cm3; anolite: 5 cm3).1 mmol of substrate was present in the catholyte (except for D-cycloserine, which was added to the catholyte after the end of the electrolysis). After 145 C (if not otherwise stated) were passed, the current was switched off and 1 mmol of alkylating agent was added to the catholyte. The solution was kept under stirring at room temperature for 2 hours, than the solvent was evaporated under reduced pressure and the residue was extracted three times with diethyl ether. The products were purified by flash column chromatography, using a mixture of ethyl acetate/light petroleum ether 2/8 in volume. The reactions on D-cycloserine were carried out following the general method, but the substrate was added to the catholyte after the end of the electrolysis. After 15 minutes at room temperature, the alkylating agent was added and the solution was kept under stirring at rt for 2 hours. The solvent was evaporated under reduced pressure and the residue was treated with 1 cm3 of saturated acqueous NaHCO3 and 1 mmol of ethyl chloroformate, at 0°C, for 2 h. The solution was then acidified with diluted HCl (pH 4) and extracted with diethyl ether. The products were purified by flash column chromatography.
  • 18
  • [ 339-72-0 ]
  • [ 386707-15-9 ]
  • methyl 3'-([(4S)-3-oxoisoxazolidin-4-yl]carbamoyl)-2,2'-binaphthalene-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; 4.3.1. Amidation General procedure: To a solution of amine (ca. 0.03 mmol) in acetonitrile (0.5 mL) was added acyl cyanide 1 (1.1 equiv) and the whole mixture was stirred at room temperature for 2-3 h under an argon atmosphere. After removal of the solvent in vacuo, the crude product was purified by silica gel chromatography to give the corresponding binaphthyl amides in 97-100% yields.
  • 19
  • [ 1449601-12-0 ]
  • [ 339-72-0 ]
YieldReaction ConditionsOperation in experiment
64% With Amberlite IR-120 PLUS ion exchange resin (sodium form) In water Inert atmosphere;
  • 20
  • recombinant methionine γ-lyase from Citrobacter freundii [ No CAS ]
  • [ 339-72-0 ]
  • (recombinant methionine γ-lyase from Citrobacter freundii)*(L-cycloserine) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ethylenediaminetetraacetic acid; DL-dithiothreitol In aq. phosphate buffer at 25℃; Pre-steady-state Stopped-flow Studies General procedure: Stopped-flow measurements with absorption detection were carried out using amodel SX20 stopped-flow spectrometer (Applied Photophysics,UK) with a 150-watt xenon lamp and a 10-mm path lengthoptical cell. The dead time of the instrument was 1.0 ms. All experiments were carried out at 25 °C in 0.1 M potassium phosphate buffer solution (pH 7.8), containing 0.5 mM DTT and 0.1mM EDTA. Solutions of enzyme (12.5 M) were mixed with various concentrations of glycine (10-500mM), L-alanine (1.0-12.0 mM), L-cycloserine (6.35-38.1 M), and L-norvaline (1.5-7.5 mM). Each kinetic curve was averaged over at least three independent experiments. The absorbance at 320, 420, and 500 nm was detected.
  • 21
  • [ 17136-54-8 ]
  • [ 339-72-0 ]
YieldReaction ConditionsOperation in experiment
With hydroxylamine hydrochloride; sodium hydroxide In methanol; water at -20 - 55℃; Large scale; 3 Preparation of crude cycloserine 11.6 parts of hydroxylamine hydrochloride and 27.4 parts of purified water was added to the glass-lined reactor, cooled to less than -10 deg.] C, was added dropwise 75.9 parts by mass fraction of 30% aqueous sodium hydroxide solution, after addition is complete, stirring for 25 ~ 35min, drops add mass fraction of 50% D- chloro-serine methyl ester hydrochloride was added dropwise during controlling the feed temperature is less than -20 deg.] C, after the addition was complete, the reaction at -20 ~ -15 0.8 ~ 1.2h, the reaction after completed, the temperature was raised to 20 ~ 30 , PH adjusted to 11 to 25 ~ 30 , the reaction 3.8 ~ 4.2h, the reaction in the process of maintaining the PH 11; raised to 50 ~ 55 , the reaction was kept 25 ~ 35min, cooling to 25 ~ 30 , adjusted PH = 11.5 ± 0.2, and concentrated under reduced pressure to below 60 condenser or a small amount of drip dropping droplets, cooled to room temperature, the reaction vessel was added 157 parts of dry methanol and stirred 25 ~ 35min , centrifuged and the cake was washed with anhydrous methanol was added, and the filtrate combined filtrate and washed by centrifugation after the reaction was poured into a tank, cooled to -5 ~ 0 , PH adjusted to 6.4 ± 0.2, 0.8 ~ 1.2h stirring crystallization , the mixing process to keep PH value is maintained at 6.4 ± 0.2, centrifugation, dry methanol soaking, washing the filter cake, the cake reserved, cold smoked and dried to give crude cycloserine.
  • 22
  • [ 474659-26-2 ]
  • [ 339-72-0 ]
  • (S)-7-methoxy-N-(3-oxoisoxazolidin-4-yl)quinoline-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% Stage #1: 7-methoxyquinoline-3-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: L-cycloserine In N,N-dimethyl-formamide 5.2. General amide bond coupling method B General procedure: N,N-Diisopropylethylamine (3.0-4.0 eq) was added to 8-methoxyquinoline-3-carboxylic acid (1.0 eq) in solvent (dichloromethane, tetrahydrofuran,or N,N-dimethylformamide, 0.05 to 0.2 M) at room temperature. Then, 1-((dimethylamino)(dimethyliminio)methyl)-1H-[1,2,3]triazolo[4,5-b]pyridine 3-oxide hexafluorophosphate(V)(1.0-1.5 eq) was added and the reaction mixture was stirred for five minutes. Then, amine (1.0 - 2.0 eq) was added and the reaction mixture was stirred for one to sixteen hours. 10% Aqueous citric acid was added and the reaction mixture was extracted with dichloromethane, washed with saturated sodium bicarbonate, dried over magnesium sulfate, filtered,and concentrated. The resulting residue was purified by RP HPLC or silica gel chromatography to give the quinoline-3-carboxamide (1%-95% yield).
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Historical Records

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[ 339-72-0 ]

Chemical Structure| 68-41-7

A170761[ 68-41-7 ]

(R)-4-Aminoisoxazolidin-3-one

Reason: Optical isomers