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[ CAS No. 68-41-7 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 68-41-7
Chemical Structure| 68-41-7
Chemical Structure| 68-41-7
Structure of 68-41-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 68-41-7 ]

CAS No. :68-41-7 MDL No. :MFCD00005353
Formula : C3H6N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :DYDCUQKUCUHJBH-UWTATZPHSA-N
M.W : 102.09 Pubchem ID :6234
Synonyms :
α-Cycloserine;RO-1-9213;Oxamycin;Orientomycin;68-41-7;Seromycin;Cycloserine;NSC 154851;NSC 76029;(R)-Cycloserine;(+)-Cycloserine;D-Cycloserine
Chemical Name :(R)-4-Aminoisoxazolidin-3-one

Calculated chemistry of [ 68-41-7 ]

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) : 0.53
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 [ 68-41-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 68-41-7 ]

* 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 [ 68-41-7 ]

[ 68-41-7 ] Synthesis Path-Downstream   1~93

  • 1
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  • [ 17143-80-5 ]
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  • [ 68-41-7 ]
  • [ 16337-02-3 ]
YieldReaction ConditionsOperation in experiment
85% With acetic acid; In ethanol; for 6h;Reflux; Acetic acid (20 ml) was added dropwise at room temperature to a solution of compound 1 (10 g, 0.10 mol)in ethanol (200 ml). The reaction mixture was refluxed for 6 h. The reaction mixture was cooled to 0-5C on an ice bath and stirring continued for 1 h. Pure product was isolated by filtration, washed with cold ethanol (5×2 ml),and dried under reduced pressure at 45C to afford product 1a. Yield 8.5 g (85%), white solid, mp 175-180C (decomp.) (mp 180C (decomp., EtOH)29). IR spectrum,nu, cm-1: 1666 (C=O), 3184-3338 (HN). 1H NMR spectrum (D2O), delta, ppm (J, Hz): 3.84 (2H, dd, J = 10.8, J = 3.2,CH2); 3.98 (2H, dd, J = 10.8, J = 4.8, CH2); 4.24 (2H, t,J = 3.6, 2CHCH2). 13C NMR spectrum (D2O), delta, ppm: 54.3(2C); 75.6 (2C); 167.8 (2C). Mass spectrum, m/z (Irel,%):205 [M+H]+ (100). Found, %: C 35.30; H 5.91; N 27.45.C6H12N4O4. Calculated, %: C 35.29; H 5.92; N 27.44.
  • 6
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  • potassium cyanate [ No CAS ]
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  • [ 39149-80-9 ]
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  • [ 708-06-5 ]
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  • [ 24424-99-5 ]
  • [ 68-41-7 ]
  • [ 128346-20-3 ]
YieldReaction ConditionsOperation in experiment
76% With triethylamine; In tetrahydrofuran; water; at 20℃; for 12h; To a stirred solution of (R) -4-aminoisoxazolidin-3-one (2.00 g, 19.59 mmol) in THF (30 mL) and water (10 mL) was added triethylamine (3.28 mL, 23.51 mmol) and Boc2O (4.55 mL, 19.59 mmol) was added. The reaction mixture was stirred at room temperature for 12 hours. The completion of the reaction was monitored by LCMS. The reaction mixture was concentrated and purified by Iscor using a 12 g silica gel column, The product was eluted with 55% ethyl acetate in petroleum ether to give (R) -tert-butyl (3-oxoisoxazolidin-4-yl) carbamate as an off-white solid (3 g, 14.84 mmol, 76% . A: Buffer: ACN (95: 5), Mobile phase B: Buffer: ACN (5:95), Method:% B: Omin. - LCMS: Buffer: 10 mM ammonium acetate adjusted to pH 5 using HCOOH, 1.7 u Method: C: Mass Lines, flow rate: 0.8 ml / min, RT-0.54 min, M (+1) -147 (t-butyl cut mass).
61% With triethylamine; In tetrahydrofuran; water; at 0 - 20℃; for 5h; Step 1 : Compound 42a (500mg, 4.9mmol) and TEA (976mg, 9.64mmol) were dissolved in a mixture of THF/water (85mL, V/V 10:7). (Boc)20 (1 Mg, 5.4mmol) was added dropwise under ice cooling. After the addition was complete, the mixture was warmed to r.t. and stirred for 5h. The mixture was evaporated to dryness and the residue was purified by column chromatography (EA:PE=3:1) to provide compound 44a (600mg, 61%) as white solid.
61% With triethylamine; In tetrahydrofuran; water; at 0 - 20℃; for 5h; Example 44 Preparation of 5-[5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid ((R)-2-ethyl-3-oxo-isoxazolidin-4-yl)-amide Preparation of (R)-4-Amino-2-ethyl-isoxazolidin-3-one Step 1: Compound 42a (500 mg, 4.9 mmol) and TEA (976 mg, 9.64 mmol) were dissolved in a mixture of THF/water (85 mL, V/V 10:7). (Boc)2O (1.17 g, 5.4 mmol) was added dropwise under ice cooling. After the addition was complete, the mixture was warmed to r.t. and stirred for 5 h. The mixture was evaporated to dryness and the residue was purified by column chromatography (EA:PE=3:1) to provide compound 44a (600 mg, 61%) as white solid.
57% With triethylamine; In tetrahydrofuran; water; at 0℃; for 5h; A solution of D-<strong>[68-41-7]cycloserine</strong> (0.50 g, 4.95 mmol) and triethylamine (0.83 mL, 5.94 mmol) in water (5 mL) was cooled in an ice bath. A solution of di-tert-butyldicarbonate (1.18 g, 5.44 mmol) in THF (25 mL) was added dropwise and the reaction mixture was stirred for 5 hours at 0 C. The solvent was removed in vacuo and the crude residue was purified by silica gel chromatography (eluent: CH2Cl2/MeOH, 98:2, v/v) to afford a white solid (0.57 g, 57%). Rf= 0.22 (CH2Cl2/MeOH,95:5 v/v), m.p. 144.2 C. [alpha]D20=+ 36.9 (c = 1, MeOH). IR (nu cm1):3313, 1716, 1677. 1HNMR (CDCl3)deltappm: 1.46 (s, 9H), 4.08 (t, J=9.1 Hz, 1H), 4.62 (m, 1H), 4.75 (m, 1H), 5.32 (br s, 1H). 13CNMR (CDCl3)deltappm: 28.4, 52.9, 75.1, 80.9, 155.8, 171.0. MS m/z225.1 [M+Na]+.

  • 19
  • [ 75-77-4 ]
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  • (R)-4-(Trimethylsilanyl-amino)-isoxazolidin-3-one [ No CAS ]
  • 20
  • [ 541-41-3 ]
  • [ 68-41-7 ]
  • 4-<(ethoxycarbonyl)amino>-3-isoxazolidinone [ No CAS ]
  • 21
  • [ 403-43-0 ]
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  • [ 144533-23-3 ]
  • 22
  • [ 2251-65-2 ]
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  • 23
  • [ 329-15-7 ]
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  • [ 144533-26-6 ]
  • 24
  • [ 126-81-8 ]
  • [ 68-41-7 ]
  • 4-<(3,3-dimethyl-5-oxo-1-cyclohexen-1-yl)amino>-3-isoxazolidinone [ No CAS ]
  • 25
  • [ 624-83-9 ]
  • [ 68-41-7 ]
  • 1-Methyl-3-((R)-3-oxo-isoxazolidin-4-yl)-urea [ No CAS ]
  • 26
  • [ 624-83-9 ]
  • [ 68-41-7 ]
  • 2-<(methylamino)carbonyl>-4-<<(methylamino)-carbonyl>amino>-3-isoxazolidinone [ No CAS ]
  • 27
  • [ 79-04-9 ]
  • [ 68-41-7 ]
  • 4-(chloroacetamido)-3-isoxazolidinone [ No CAS ]
  • 2-(chloroacetyl)-4-(chloroacetamido)-3-isoxazolidinone [ No CAS ]
  • 28
  • [ 701-99-5 ]
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  • [ 115042-43-8 ]
  • 29
  • [ 1711-07-5 ]
  • [ 68-41-7 ]
  • [ 144533-22-2 ]
  • 30
  • [ 123-54-6 ]
  • [ 68-41-7 ]
  • (R)-4-<(1-methyl-3-oxo-1-butenyl)amino>-3-isoxazolidinone [ No CAS ]
  • 31
  • [ 2719-27-9 ]
  • [ 68-41-7 ]
  • 4-<(cyclohexylcarbonyl)amino>-3-isoxazolidinone [ No CAS ]
  • 32
  • [ 407-25-0 ]
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  • [ 144533-21-1 ]
  • 33
  • [ 68-41-7 ]
  • [ 312-94-7 ]
  • [ 144533-24-4 ]
  • 34
  • [ 68-41-7 ]
  • [ 3019-71-4 ]
  • 1-(3-oxo-4-isoxazolidinyl)-3-(trichloroacetyl)urea [ No CAS ]
  • 36
  • [ 82911-69-1 ]
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  • [ 219829-12-6 ]
  • 39
  • [ 7732-18-5 ]
  • [ 67-64-1 ]
  • [ 68-41-7 ]
  • [ 17143-80-5 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 1 Phthaloylation of D-cycloserine with N-carboethoxyphthalimide D-cycloserine (15.3 g, 0.15 moles) and sodium carbonate (15.9 g, 0.15 mole) were dissolved in 200 ml of water. N-carboethoxyphthalimide (36.0 g, 0.164 mole) was added to the solution and the mixture was stirred for 25 minutes and filtered to remove unreacted N-carboethoxyphthalimide (12.1 g). The filtrate was chilled on ice and acidified with 4N HCl. Phthaloyl-D-cycloserine (18.5 g) precipitated out of solution and was collected by filtration, air dried, and recrystallized from ethyl acetate.
EXAMPLE 1 Phthaloylation of D-cycloserine with N-carboethoxyphthalimide D-cycloserine (15.3 g, 0.15 mol) and sodium carbonate (15.9 g, 0.15 mol) were dissolved in 200 ml of water. N-Carboethoxyphthalimide (36.0 g, 0.164 mol) was added to the solution and the mixture was stirred at room temperature for 25 minutes and filtered to remove unreacted N-carboethoxyphthalimide (12.1 g). The filtrate was chilled on ice bath and acidified with 4N HCl. Phthaloyl-D-cycloserine (18.5 g) precipitated out of solution and was collected by filtration, air dried, and recrystallized from ethyl acetate.
EXAMPLE 1 Phthaloylation of D-cycloserine with N-carboethoxyphthalimide D-cycloserine (15.3 g, 0.15 mol) and sodium carbonate (15.9 g, 0.15 mol) were dissolved in 200 ml of water. N-carboethoxyphthalimide (36.0 g, 0.164 mol) was added to the solution and the mixture was stirred for 25 minutes and then filtered to remove unreacted N-carboethoxyphthalimide (12.1 g). The filtrate was chilled on ice bath and acidified with 4N HCl. Phthaloyl-D-cycloserine (18.5 g) precipitated out of solution and was collected by filtration, air dried, and recrystallized from ethyl acetate.
cephalasporins, chalcomycin, chlorotetracycline, chromomycin, condicidin, cycloserine, endomycin, erythromycin, furacin, gentamicin,
Other Cell-Wall Synthesis Inhibitors bacitracin cycloserine fosfomycin (Monurol) vancomycin (Vancocin)

  • 41
  • 3-chloro-D-alanine methyl ester hydrochloride [ No CAS ]
  • [ 68-41-7 ]
  • 42
  • 3-chloro-<i>N</i>-trifluoroacetyl-D-alanine hydroxyamide [ No CAS ]
  • [ 68-41-7 ]
  • 43
  • DL-cycloserine [ No CAS ]
  • [ 68-41-7 ]
  • 44
  • <i>O</i>-amino-D-serine methyl ester dihydrochloride [ No CAS ]
  • [ 68-41-7 ]
  • 45
  • (<i>R</i>)-4-acetylamino-isoxazolidin-3-one [ No CAS ]
  • [ 68-41-7 ]
  • 46
  • [ 7732-18-5 ]
  • [ 68-41-7 ]
  • [ 16337-02-3 ]
  • 47
  • [ 128346-20-3 ]
  • [ 68-41-7 ]
  • 48
  • 4-amino-4,5-dihydroisoxazol-3-yl acetate [ No CAS ]
  • [ 68-41-7 ]
  • 49
  • [ 500220-18-8 ]
  • [ 68-41-7 ]
  • 50
  • 4-amino-4,5-dihydroisoxazol-3-yl octanoate [ No CAS ]
  • [ 68-41-7 ]
  • 51
  • 4-amino-4,5-dihydroisoxazol-3-yl laurate [ No CAS ]
  • [ 68-41-7 ]
  • 52
  • [ 500220-19-9 ]
  • [ 68-41-7 ]
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  • [ 500220-20-2 ]
  • [ 68-41-7 ]
  • 54
  • 4-amino-4,5-dihydroisoxazol-3-yl oleate [ No CAS ]
  • [ 68-41-7 ]
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  • [ 500220-21-3 ]
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  • [ 51300-90-4 ]
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  • [ 128346-20-3 ]
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  • [ 452105-55-4 ]
  • [ 68-41-7 ]
  • [ 1013920-74-5 ]
YieldReaction ConditionsOperation in experiment
87.6% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; Example 42: Preparation of 5-[5-Fluoro-2-oxo-l,2-dihydro-indol-(3Z)- yIidenemethyl]-2,4-dimethyI-lH-pyrrole-3-carboxylic acid [(R)-2-(2-hydroxy- ethyI)-3-oxo-isoxazolidin-4-yl]-amidePreparation of 5-[5-Fluoro-2-oxo-l ,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4- dimethyl- 1 H-pyrrole-3-carboxylic acid ((R)-3-oxo-isoxazolidin-4-yl)-amide (42b)42a 42bTo the solution of A4 (1.75g, 4.2mmol) and DIEA (2.5g, 17mmol) in 15OmL of DMF, was added compound 42a (800mg, S.lmmol). The reaction mixture was stirred at room temperature for several hours. LC/MS was applied to determine completion of the reaction. DMF was evaporated under reduced pressure and the residue was precipitated with 5% diethylamine/methanol (50OmL) under sonication. The solid was collected by filtration and washed with methanol, dried under vacuum to provide to provide 42b (1.41g, 87.6% yield): 1H NMR (300 MHz, DMSO-d6): delta=13.68(s, 1 H),10.88(S,1 H), 7.71-7.77(m, 3H), 7.41(s, IH), 6.82-6.96(m, 2H), 4.08- 4.13(m, IH), 3.06-3.13(m, IH), 2.41-2.45(ds, 6H), 2.25-2.31(m, 2H), 1.79-1.98(m, 3H). LC/MS: 395.3 [M-H]+.
87.6% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; Example 42 Preparation of 5-[5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole3-carboxylic acid [(R)-2-(2-hydroxy-ethyl)-3-oxo-isoxazolidin-4-yl]-amide Preparation of 5-[5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid ((R)-3-oxo-isoxazolidin-4-yl)-amide (42b) To the solution of A4 (1.75 g, 4.2 mmol) and DIEA (2.5 g, 17 mmol) in 150 mL of DMF, was added compound 42a (800 mg, 5.1 mmol). The reaction mixture was stirred at room temperature for several hours. LC/MS was applied to determine completion of the reaction. DMF was evaporated under reduced pressure and the residue was precipitated with 5% diethylamine/methanol (500 mL) under sonication. The solid was collected by filtration and washed with methanol, dried under vacuum to provide to provide 42b (1.41 g, 87.6% yield): 1H NMR (300 MHz, DMSO-d6): delta=13.68(s, 1H),10.88(s,1H), 7.71-7.77(m, 3H), 7.41(s, 1H), 6.82-6.96(m, 2H), 4.08-4.13(m, 1H), 3.06-3.13(m, 1H), 2.41-2.45(ds, 6H), 2.25-2.31(m, 2H), 1.79-1.98(m, 3H). LC/MS: 395.3 [M-H]+.To the solution of 42b (1.0 eq.) cooled on ice bath was added NaH (4.0 or 1.5 eq.). The resulting mixture was stirred for an hour and was then added 2-bromoethanol (3 eq.), the reaction mixture was stirred at room temperature for several hours. LC/MS detection was applied to determine completion of the reaction. DMF was evaporated under reduced pressure and the residue was precipitated with 5% diethylamine/methanol under sonication. The solid was collected by filtration, washed with methanol twice, and further purified by Prep-LC to obtain the title compound (18 mg, 11%yield) as orange solids: 1H NMR (300 MHz, DMSO-d6): delta=13.70(s, 1H), 10.91(s, 1H), 8.08-8.10(d, 1H), 7.72-7.79(m, 2H), 6.82-6.97(m, 2H), 5.01-5.10(q, 1H), 4.79-4.81(t, 1H), 4.56-4.62(t, 1H), 4.02-4.08(q, 1H), 3.49-3.63(m, 4H), 2.41-2.43(ds, 6H). LC/MS: 428.9 [M+H]+.
  • 59
  • [ 1336-21-6 ]
  • [ 68-41-7 ]
  • D-2-Amino-3-(aminooxy)propionic acid dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In hydrogenchloride; EXAMPLE 7 D-2-Amino-3-(aminooxy)propionic acid dihydrochloride (6) <strong>[68-41-7]D-<strong>[68-41-7]Cycloserine</strong></strong> (5, 408 mg. 4 mmol) was dissolved in 2N HCl (20 mL); the resulting solution was kept at 60 C. for 6 h. After cooling to 0 C., the solution was adjusted to pH 4.5 with 15% (w/v) NaOH and was applied to a 25 cm3 Dowex 50*8 (H+) column. The resin was washed with deionized water (500 mL) followed by 5N NH4 OH (80 mL). The column effluent was concentrated by rotary evaporation in vacuo to give 6 (480 mg, 99% yield) as a colorless solid, m.p. 167.0-169.5 C.; [alpha]D23 =+24.5 (c=2.15, H2 O); 1 H-NMR (D2 O); delta4.79 (dd, J=11.0, 5.2 Hz, 1H, 3-CH2a) 4.62 (dd, J=11.0, 3.0 Hz, 1H, 3-CH2b), 4.55 (dd, J=5.2, 3.0 Hz, 1H, 2-CH) ppm; 13 C-NMR (D2 O): delta170.95 (C-1), 74.19 (C-3), 54.41 (C-2) ppm; Anal (C3 H10 Cl2 N2 O3) C, H, N, Cl.
  • 60
  • [ 209736-68-5 ]
  • [ 68-41-7 ]
  • [1S-[1αa(S*),2β,3β,4α]]-4-[7-(Butylamino)-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]-N-(tetrahydro-3-oxo-isoxazol-4-yl)-2,3-dihydroxy-cyclopentanecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 25 [1S-[1alphaa(S*),2beta,3beta,4alpha]]-4-[7-(Butylamino)-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]-N-(tetrahydro-3-oxo-isoxazol-4-yl)-2,3-dihydroxy-cyclopentanecarboxamide Prepared according to the method of Example 20 step (a) using the product of Example 2 and D-<strong>[68-41-7]cycloserine</strong>. Melting point: 209-211 C. (EtOAc); MS (APCI) 495 (M+H+, 100%); NMR deltaH (d6-DMSO) 11.53 (1H, s), 9.01 (1H, t), 8.55 (1H, d), 5.16 (1H, d), 5.03 (1H, d), 4.98 (1H, q), 4.78 (1H, m), 4.55 (1H, t), 4.42 (1H, q), 4.11 (1H, m), 3.95 (1H, t), 3.49 (2H, q), 3.10 (2H, m), 2.83 (1H, m), 2.39 (1H, m), 2.27 (1H, m), 1.70 (2H, m), 1.60 (2H, m), 1.34 (2H, m), 0.99 (3H, t), 0.91 (3H, t).
  • 61
  • [ 68-41-7 ]
  • β-aminoxy-D-alanine dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
In hydrogenchloride; (a) 2 g of D-<strong>[68-41-7]cycloserine</strong> was dissolved in 11 ml of 50% conc. hydrochloric acid, and acid hydrolyzed at 60 C. for 3 hours. After the completion of the reaction, the reaction mixture was concentrated under reduced pressure, azeotropically distilled with ethanol several times, and dried under reduced pressure overnight to obtain beta-aminoxy-D-alanine dihydrochloride.
In hydrogenchloride; (a) 2 g of D-<strong>[68-41-7]cycloserine</strong> was dissolved in 11 ml of 50 % conc. hydrochloric acid, and acid hydrolyzed at 60oC for 3 hours. After the completion of the reaction, the reaction mixture was concentrated under reduced pressure, azeotropically distilled with ethanol several times, and dried under reduced pressure overnight to obtain beta-aminoxy-D-alanine dihydrochloride.
  • 62
  • [ 123-54-6 ]
  • [ 68-41-7 ]
  • [ 785004-20-8 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 1 A mixture of about 3.0 g. of D-4-amino-3-isoxazolidinone and 30 ml. of 2,4-pentanedione is stirred in a dry atmosphere at approximately room temperature for about 2 days. The D-4-amino-3-isoxazolidinone gradually goes into solution; and the reaction product, which crystallizes from the reaction solution, is recovered by filtration, washed with three 20 ml.-portions of ether, and dried at room temperature in vacuo to give about 3.5 g. of D-4-(1'-methyl-3'-oxo-1'-butenyl)amino-3-isoxazolidinone; m.p. 145C. dec.; alphaD27 = -159 (1% methanol).
  • 63
  • [ 815-57-6 ]
  • [ 68-41-7 ]
  • D-4-(1',2'-dimethyl-3'-oxo-1'-butenyl)amino-3-isoxazolidinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 3 A mixture of about 2.0 g. of D-4-amino-3-isoxazolidinone and 10 ml. of 3-methyl-2,4-pentanedione is stirred in a dry atmosphere at approximately room temperature for a period of about 42 hours. The D-4-amino-3-isoxazolidinone gradually goes into solution; and the reaction product, which crystallizes from the reaction solution, is recovered by filtration, washed with five 5 ml.-portions of ether, and dried at room temperature in vacuo to give about 2.0 g. of D-4-(1',2'-dimethyl-3'-oxo-1'-butenyl)amino-3-isoxazolidinone; m.p. 121.5-123.5C.
  • 64
  • [ 773103-94-9 ]
  • [ 68-41-7 ]
  • 3-[5-bromo-4-(2,4-difluoro-benzyloxy)-2-methyl-6-oxo-6H-pyrimidin-1-yl]-4-methyl-N-((R)-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; 3-[5-Bromo-4-(2,4-difluoro-benzyloxy)-2-methyl-6-oxo-6H-pyrimidin-1-yl]-4- methyl-benzoic acid (40 mg, 0.086 mmol), D-<strong>[68-41-7]cycloserine</strong> (16 mg, 0.16 mmol), HATU (37 mg, 0.097 mmol), DIEA (18 mul, 0.10 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 MHz, d6-DMSO) delta 11.57 (br s, 1H), 9.00 (m, 1H), 7.94-7.92 (m, 1 H), 7.84-7.83 (m, 1 H), 7.70-7.64 (m, 1 H), 7.57 (d, J = 8.00 Hz, 1 H), 7.34 (dt, J = 2.1, 10.0 Hz, 1 H), 7.17 (dt, J = 2.1, 8.5 Hz, 1H), 5.56 (d, J = 12.0 Hz, 1H), 5.48 (d, J = 12.4 Hz, 1 H), 5.08-5.02 (m, 1 H), 4.58 (dt, J = 3.1 , 8.5 Hz, 1 H), 4.08 (q, J = 9.1 Hz, 1H), 2.12, 2.11 (2s, 3H), 2.08 (s, 3H); MS (m/z): 549, 551 [M+ 1]+.
  • 65
  • copper(ll) sulfate pentahydrate [ No CAS ]
  • sodium perchlorate [ No CAS ]
  • [ 68-41-7 ]
  • Cu(2+)*CH2CHNH2CONO(1-)*ClO4(1-)*4H2O=Cu(CH2CHNH2CONO)ClO4*4H2O [ No CAS ]
  • 66
  • [ 6046-93-1 ]
  • [ 68-41-7 ]
  • Cu(2+)*2CH2CHNH2CONO(1-)*2H2O=Cu(CH2CHNH2CONO)2*2H2O [ No CAS ]
  • 67
  • [ 12093-10-6 ]
  • [ 68-41-7 ]
  • C10H9FeCHNC3H4NO2 [ No CAS ]
  • 68
  • copper(ll) sulfate pentahydrate [ No CAS ]
  • [ 68-41-7 ]
  • Cu(2+)*2CH2CHNH2CONO(1-)*2H2O=Cu(CH2CHNH2CONO)2*2H2O [ No CAS ]
  • 69
  • [ 4795-29-3 ]
  • [ 7154-73-6 ]
  • [ 2038-03-1 ]
  • [ 4572-03-6 ]
  • [ 27757-85-3 ]
  • [ 109-12-6 ]
  • [ 3731-53-1 ]
  • [ 107-10-8 ]
  • [ 7663-77-6 ]
  • [ 6628-04-2 ]
  • [ 2620-50-0 ]
  • polystyrene carboxaldehyde resin [ No CAS ]
  • [ 5071-96-5 ]
  • [ 617-89-0 ]
  • [ 28466-26-4 ]
  • [ 42185-03-5 ]
  • [ 453-71-4 ]
  • [ 19293-58-4 ]
  • [ 75-04-7 ]
  • [ 62-53-3 ]
  • [ 1003-03-8 ]
  • [ 51387-90-7 ]
  • [ 74-89-5 ]
  • [ 100-46-9 ]
  • [ 4152-90-3 ]
  • [ 68-41-7 ]
  • C9H8FN2O3Pol [ No CAS ]
  • C10H10FN2O3Pol [ No CAS ]
  • C11H12FN2O3Pol [ No CAS ]
  • C14H10FN2O3Pol [ No CAS ]
  • C11H8FN4O3Pol [ No CAS ]
  • C12H8FN4O3Pol [ No CAS ]
  • C13H10FN2O4Pol [ No CAS ]
  • C15H12FN2O3Pol [ No CAS ]
  • C14H11FN3O3Pol [ No CAS ]
  • C13H14FN2O3Pol [ No CAS ]
  • C13H10FN2O3PolS [ No CAS ]
  • C13H16FN2O4Pol [ No CAS ]
  • C13H14FN2O4Pol [ No CAS ]
  • C16H14FN2O4Pol [ No CAS ]
  • C11H9FN3O5Pol [ No CAS ]
  • C15H11ClFN2O3Pol [ No CAS ]
  • C17H17FN3O3Pol [ No CAS ]
  • C14H17FN3O3Pol [ No CAS ]
  • C14H17FN3O4Pol [ No CAS ]
  • C15H19FN3O3Pol [ No CAS ]
  • C16H12FN2O5Pol [ No CAS ]
  • C18H13FN3O3Pol [ No CAS ]
  • C15H17FN3O4Pol [ No CAS ]
  • C16H22FN4O3Pol [ No CAS ]
YieldReaction ConditionsOperation in experiment
A library of compounds in which R4 was various groups having the formula [CONHR »] was prepared by the process described above using 4-fluoro-3-nitrobenzoic acid, as follows: [72] Aldehyde resin was mixed with a primary amine (R17-NH2) in [DICHLOROETHANE] (DCE), triethylorthoformate (TEOF), and DMF (containing [1%] acetic acid) in a 1: 1: 1 ratio. After shaken overnight, sodium triacetoxyborohydride (20 eq. ) dissolved in DMF was added (Abdel-Magid, A. F. , et al., Tetrahedron Lett, 3 1: 5595-5598 (1990) ). After the mixture was shaken at room temperature overnight, the resin was filtered and washed with DMF (3 x 5 mL), [MEOH] [(3 X 5] mL), DMF [(3 X 5] mL), [MEOH] [(3 X 5] mL), and [CH2CL2] [(3 X 5] mL). The resin was washed twice with 5 mL DMF containing [1%] Hunig's base. To the filtered resin was added a mixture of 4-fluoro-3-nitrobenzoic acid (FNBA, 10 eq. ) and diisopropylcarbodiimide (DIC, 5 eq. ) in 2: 1 DMF : DCM. After shaking at room temperature overnight, the resin was filtered and washed with DMF (3 x 5 mL) and [CH2C12] (3 x 5 mL). [73] The resin was shaken with a primary amine [(R2-NH2)] in DMF for 8 hrs, filtered, and washed with DMF (6 x 5 mL), [MEOH] [(3 X 5] mL), and CH2C12 (3 x 5 mL). The aryl nitro group was reduced by the addition of tin (II) chloride dihydrate (20 eq. , >2 M) and N-methyl morpholine (NMM, 20 eq. ) in N-methyl pyrrolidinone (NMP). After shaken at room temperature overnight, the resin was filtered and washed with NMP (3 x 5 mL), [MEOH] (3 x 5 mL), and [CH2CI2 (3 X 5] mL). The resulting resin was shaken at room temperature with cyanogen bromide (5 eq. ) overnight, filtered, and washed with CH2Cl2 (3 x 5 mL), [MEOH] (3 x 5 mL), and CH2CI2 (3 x 5 mL). To produce a free amine, the resin was shaken for 30 min. in CHCl2 with the addition of sodium methoxide in methanol, filtered, and washed with CH2Cl2 [(4 X 5] mL). [[74]] In the final diversification step, the resin was heated at 500 C in DMF with a mono- substituted epoxide [[RLCH (-CH2O-)].] After shaking for 2 to 4 days the resin was filtered and washed with DMF (5 x 5 mL), [MEOH] [(3 X 5] mL), and CH2Cl2 (3 x 5 mL). T he resin-bound benzimidazole was cleaved from the solid-support by treatment with TFA: [CH2C12] (2: 3) for 1 hour at room temperature.
  • 71
  • [ 98-09-9 ]
  • [ 68-41-7 ]
  • [ 1248593-33-0 ]
  • 72
  • [ 120883-74-1 ]
  • [ 68-41-7 ]
  • 73
  • [ 34446-64-5 ]
  • [ 68-41-7 ]
  • [ 1268243-03-3 ]
  • 74
  • 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)isoxazol-3-yl]-2-methylbenzoyl chloride [ No CAS ]
  • [ 68-41-7 ]
  • [ 1309957-71-8 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In toluene; at 50℃; for 16h; D-<strong>[68-41-7]cycloserine</strong> (21 mg) was added to a solution of the acid chloride (45mg) and triethylamine (0.1 ml) in toluene (2 ml). The reaction mixture was stirred at 50 C for 16 hours. The reaction mixture was diluted with water and ethyl acetate and the phases were separated. The organic phase was washed twice with water, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (eluent: dichloromethane / methanol 5%) to give the title compound (28 mg) as a colorless solid. 1H-NMR (CDC13, 400 MHz): 8.60 (s, br., 1H), 7.60-7.45 (m, 6H), 6.40 (s, 1H), 5.05 (m, 1H), 4.85 (m, 1H), 4.20 (t, 1H), 4.05 (d, 1H), 3.70 (d, 1H), 2.50 (s, 3H) ppm.
  • 75
  • [ 1360187-62-7 ]
  • 2-aminoacrylic acid methyl ester [ No CAS ]
  • [ 68-41-7 ]
YieldReaction ConditionsOperation in experiment
39%; 48% With hydroxylamine hydrochloride; sodium methylate; In methanol; water; at 0 - 20℃; for 9h; Sodium methoxide (5.477 mmol) in MeOH was added to a solution of hydroxylamine hydrochloride (127 mg, 1.83 mmol) in MeOH (10 mL) and stirred at room temperature for 30 min. The mixture was cooled to 0 C, and sodium chloride was filtered. A solution of compound 10 (320 mg, 1.12 mmol) in H2O (10 mL) was added to the filtrate at 0 C. The mixture was stirred at 0 C for 5 h and stirred at room temperature for 4 h. 40 mL of ethanol/isopropy alcohol was added. The precipitate salts were filtered, and the filtrated was cooled to 0 C in the ice bath. Glacial acetic acid was added dropwise to the well-stirred mixture to reach pH 6.0 and yielded a colorless solid. The crystalline precipitate was filtered and washed twice with 1:1 ethanol/isopropyl alcohol and diethyl ether to give d-4-amino-3-isoxazolidinone (55 mg, 48%).
  • 76
  • [ 144533-21-1 ]
  • [ 68-41-7 ]
YieldReaction ConditionsOperation in experiment
315 mg With water; sodium hydroxide; In methanol; dichloromethane; at 20℃; for 4h; Sodium methoxide (12.27 mmol) in MeOH was added to a solution of hydroxylamine hydrochloride (465 mg, 6.69 mmol) in MeOH (10 mL). The mixture was stirred at room temperature for 30 min and cooled to 0 C. Then the sodium chloride was filtered. A solution of compound 3 (1.2 g, 5.58 mmol) in CH3CN (20 mL) was added to the filtrate at 0 C. The mixture was stirred at 0 C for 4 h and concentrated under reduced pressure. Et3N (1.16 mL, 8.37 mmol) and CH2Cl2 (30 mL) was added to the mixture and stirred at 0 C for 10 min. Methanesulfonyl chloride (0.73 g, 6.14 mmol) was added next, and the mixture was stirred at 0 C for 1 h. DBU (1.27 g, 8.37 mmol) was added to the mixture at 0 C and stirred at room temperature for 2 d. After NaOH (1.12 g, 27 mmol) in water (20 mL) and MeOH (20 mL) were added, the mixture was stirred at room temperature for 4 h. 50 mL of ethanol/isopropyl alcohol was added. The precipitate salts were filtered, and the filtrated was cooled to 0 C in the ice bath. Glacial acetic acid was added dropwise to the well-stirred mixture to reach pH 6.0 and gave a colorless solid. The crystalline precipitate was filtered and washed twice with 1:1 ethanol/isopropyl alcohol and diethyl ether to give d-4-amino-3-isoxazolidinone (315 mg, 55%). mp 146-148 C; +110 (c 1.0, H2O); 1H NMR (DMSO-d6, 300 MHz) delta 4.38 (t, 1H), 3.51 (m, 2H); 13C NMR (DMSO-d6, 75 MHz) delta 174.5, 75.1, 53.6; HRMS (ESI) m/z (M+H)+ calcd for C3H6N2O2 = 102.0919, found 102.0743.
121 mg With water; sodium hydroxide; In methanol; at 20℃; for 4h; Hydrazine (0.173 mL, 4.17 mmol) was added to a solution of compound 7 (0.5 g, 1.39 mmol) in MeOH (20 mL) and CH2Cl2 (20 mL) and stirred at room temperature for 3 h. Aqueous 5% NaHCO3 was added to neutralize the reaction mixture, and the mixture was concentrated under reduced pressure. The crude residue was dissolved in MeOH (20 mL) and CH2Cl2 (20 mL), and KCN (18 mg, 0.28 mmol) was added to the reaction mixture. The mixture was stirred at room temperature for 4 h, followed by the addition of NaOH (0.39 g, 9.72 mmol) in water (20 mL) and MeOH (20 mL). The mixture was stirred at room temperature for 4 h. After 50 mL of ethanol/isopropyl alcohol was added, the precipitate salts were filtered, and the filtrated was cooled to 0 C in the ice bath. Glacial acetic acid was added dropwise to the well-stirred mixture to reach pH 6.0 and gave a colorless solid. The crystalline precipitate was filtered and washed twice with 1:1 ethanol/isopropyl alcohol and diethyl ether to give d-4-amino-3-isoxazolidinone (121 mg, 85%).
10.8 g With water; sodium hydroxide; at 20℃; for 4.5h; The concentrated solution obtained in the above step (3) is added to 300 ml of 15% sodium hydroxide solution. Stir and hydrolyze 4.5h at room temperature. Add 200ml of ethanol: isopropyl alcohol = 1:1 mixed solvent, The precipitated salt was removed by filtration and the filtrate was cooled in an ice bath. Under stirring, glacial acetic acid was added dropwise to adjust the pH of the reaction mixture to 6.0. Precipitation, filtration, Separately use 200ml of ethanol: isopropanol = 1:1 Wash with 200ml petroleum ether 1 or 2 times, 10.8 g of D-cycloserine was obtained with an overall yield of 56.2% and a content of 98% or more.
  • 77
  • [ 109-65-9 ]
  • [ 68-41-7 ]
  • C7H14N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: Constant current electrolyses (I = 25 mA cm-2) were performed under a nitrogen atmosphere, at 20C, 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-<strong>[68-41-7]cycloserine</strong>, 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-<strong>[68-41-7]cycloserine</strong> 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 0C, 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.
  • 78
  • [ 111-83-1 ]
  • [ 68-41-7 ]
  • C11H22N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: Constant current electrolyses (I = 25 mA cm-2) were performed under a nitrogen atmosphere, at 20C, 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-<strong>[68-41-7]cycloserine</strong>, 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-<strong>[68-41-7]cycloserine</strong> 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 0C, 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.
  • 79
  • [ 2969-81-5 ]
  • [ 68-41-7 ]
  • C9H16N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: Constant current electrolyses (I = 25 mA cm-2) were performed under a nitrogen atmosphere, at 20C, 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-<strong>[68-41-7]cycloserine</strong>, 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-<strong>[68-41-7]cycloserine</strong> 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 0C, 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.
  • 80
  • [ 459-46-1 ]
  • [ 68-41-7 ]
  • C10H11FN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: Constant current electrolyses (I = 25 mA cm-2) were performed under a nitrogen atmosphere, at 20C, 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-<strong>[68-41-7]cycloserine</strong>, 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-<strong>[68-41-7]cycloserine</strong> 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 0C, 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.
  • 81
  • [ 20443-98-5 ]
  • [ 68-41-7 ]
  • [ 1399847-93-8 ]
YieldReaction ConditionsOperation in experiment
88% General procedure: Constant current electrolyses (I = 25 mA cm-2) were performed under a nitrogen atmosphere, at 20C, 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-<strong>[68-41-7]cycloserine</strong>, 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-<strong>[68-41-7]cycloserine</strong> 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 0C, 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.
  • 82
  • [ 402-49-3 ]
  • [ 68-41-7 ]
  • C11H11F3N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: Constant current electrolyses (I = 25 mA cm-2) were performed under a nitrogen atmosphere, at 20C, 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-<strong>[68-41-7]cycloserine</strong>, 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-<strong>[68-41-7]cycloserine</strong> 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 0C, 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.
  • 83
  • C8H8F6N2O5 [ No CAS ]
  • [ 68-41-7 ]
YieldReaction ConditionsOperation in experiment
233 mg With water; sodium hydroxide; In methanol; at 20℃; for 6h; Et3N (0.79 mL, 5.65 mmol) was added to a solution of compound 3 (0.9 g, 4.19 mmol) in CH2Cl2 (20 mL) and stirred at 0 C for 10 min. Methanesulfonyl chloride (0.55 g, 4.81 mmol) was added and the mixture was stirred at 0 C for 1 h and warmed to room temperature with stirring for 1 h. After stirring the solution of DBU (0.94 mL, 6.28 mmol) and trifluoroacetohydroxamic acid (0.76 g, 5.86 mmol) in CH2Cl2 (30 mL) to 0 C for 30 min, the mixture of DBU and trifluoroacetohydroxamic acid was added to crude mesylate solution at 0 C. The mixture was stirred at 0 C for 1 h and warmed to room temperature with stirring for 2 d. After the addition of NaOH (1.12 g, 27 mmol) in water (40 mL) and MeOH (40 mL), the mixture was stirred at room temperature for 6 h. 50 mL of ethanol/isopropyl alcohol was added. The precipitated salts were filtered, and the filtrate was cooled to 0 C in an ice bath. Glacial acetic acid was added dropwise to the well-stirred mixture to reach pH of 6.0 and then gave a colorless solid. The crystalline precipitates were filtered and washed twice with 1:1 ethanol/isopropyl alcohol and diethyl ether to give d-4-amino-3-isoxazolidone (233 mg, 55%). m.p. 146-148 C; = +110 (c 1.0, H2O); 1H NMR (DMSO-d6, 300 MHz) delta 4.38 (t, 1H), 3.51 (m, 2H); 13C NMR (DMSO-d6, 75 MHz) delta 174.5, 75.1, 53.6; HRMS (ESI) m/z (M+H)+ calcd for C3H6N2O2 = 102.0919, found 102.0927.
  • 84
  • C6H8F3NO7S [ No CAS ]
  • [ 68-41-7 ]
YieldReaction ConditionsOperation in experiment
341 mg With hydroxylamine hydrochloride; water; sodium hydroxide; In methanol; at 60℃; for 8h; Chlorosulfonic acid (0.72 g, 6.14 mmol) was added to a solution of compound 3 (1.1 g, 5.12 mmol) in Et2O (40 mL) at 0 C. The mixture was stirred at 0 C for 4 h. After sodium hydroxide (1.02 g, 25.57 mmol) was added to hydroxylamine hydrochloride (0.49 g, 7.16 mmol) in H2O (50 mL) and MeOH (50 mL) and stirred at room temperature for 5 min, the mixture of hydroxylamine was added to the solution of sulfonic acid compound. The mixture was stirred at 0 C for 2 h and then stirred at 60 C for 8 h. The reaction mixture was neutralized with AcOH and concentrated under reduced pressure. 60 mL of ethanol/isopropyl alcohol was added. The precipitated salts were filtered, and the filtrate was cooled to 0 C in an ice bath. Glacial acetic acid was added dropwise to the well-stirred mixture to reach pH of 6.0, giving a colorless solid. The crystalline precipitates were filtered and washed twice with 1:1 ethanol/isopropyl alcohol and diethyl ether to give d-4-amino-3-isoxazolidone 341 mg, 65%).
  • 85
  • [ 120883-74-1 ]
  • [ 68-41-7 ]
YieldReaction ConditionsOperation in experiment
494 mg With lithium hydroxide; In methanol; water; at 0℃; for 5h; Sodium methoxide (0.806 g, 14.92 mmol) was added to hydroxylamine hydrochloride (0.57 g, 8.14 mmol) in H2O (50 mL) and MeOH (50 mL) and stirred for 5 min. The solution of hydroxylamine was added to the compound 9 (1.2 g, 6.78 mmol) and stirred at room temperature for 10 min. Lithium hydroxide (0.65 g, 27.13 mmol) was added at 0 C. The mixture was stirred at 0 C for 5 h. The reaction mixture was neutralized with AcOH and then concentrated under reduced pressure. 60 mL of ethanol/isopropyl alcohol was added. The precipitated salts were filtered, and the filtrate was cooled to 0 C in an ice bath. Glacial acetic acid was added dropwise to the well-stirred mixture to reach pH of 6.0 and gave a colorless solid. The crystalline precipitates were filtered and washed twice with 1:1 ethanol/isopropyl alcohol and diethyl ether to give d-4-amino-3-isoxazolidone (494 mg, 71%).
  • 86
  • [ 68-41-7 ]
  • [ 386707-15-9 ]
  • methyl 3'-([(4R)-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; 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.
  • 87
  • [ 864725-62-2 ]
  • [ 68-41-7 ]
  • [ 1309957-71-8 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 2 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-((R)-3-oxo-isoxazolidin-4-yl)-benzamide (compound B1) Oxalyl chloride (0.122 ml) was added to a solution of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid (0.5 g) (prepared according to WO 2009/080250) in dichloromethane (3 ml). After addition of two drops of N,N-dimethylformamide ("DMF?) the reaction mixture was stirred at ambient temperature for 18 hours. The reaction mixture was concentrated to give the acid chloride as a yellow solid, which was used in the next step without further purification. D-<strong>[68-41-7]cycloserine</strong> (21 mg) was added to a solution of the acid chloride (45 mg) and triethylamine (0.1 ml) in toluene (2 ml). The reaction mixture was stirred at 50 C. for 16 hours. The reaction mixture was diluted with water and ethyl acetate and the phases were separated. The organic phase was washed twice with water, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (eluent: dichloromethane/methanol 5%) to give the title compound (28 mg) as a colorless solid. 1H-NMR (CDCl3, 400 MHz): 8.60 (s, br., 1H), 7.60-7.45 (m, 6H), 6.40 (s, 1H), 5.05 (m, 1H), 4.85 (m, 1H), 4.20 (t, 1H), 4.05 (d, 1H), 3.70 (d, 1H), 2.50 (s, 3H) ppm.
  • 88
  • [ 933451-71-9 ]
  • [ 68-41-7 ]
  • [ 1415242-26-0 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 87h; <strong>[68-41-7]D-<strong>[68-41-7]Cycloserine</strong></strong> (0.58 g) was added to a solution of 4-[3-(3,5-dichlorophenyl)-3,4-dihydro-3- (trifluoromethyl)-2H-pyrrol-5-yl]-2-methyl-benzoic acid, (1 g) (prepared according to WO 2010/020522) in NN-dimethylformamide ("DMF") (20 ml), followed by the addition of Hunig's base (1.9 ml), hydroxybenzotriazole (HOBT) (0.28 g) and l-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC1) (0.54 g). The reaction mixture was stirred at ambient temperature for 63 hours. Further NN-dimethylformamide ("DMF") (10 ml) was added and the reaction mixture was stirred at ambient temperature for another 24 hours.The reaction mixture was diluted with water and extracted 3 times with ethyl acetate. The organic phases were combined, washed twice with water, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (eluent: dichloromethane / methanol) to give the title compound (135 mg) as a colorless solid.
  • 89
  • [ 34619-03-9 ]
  • [ 68-41-7 ]
  • [ 128346-20-3 ]
YieldReaction ConditionsOperation in experiment
157 g With triethylamine; In tetrahydrofuran; water; at 10℃; 30 D-<strong>[68-41-7]cycloserine</strong> (100 g) was dissolved in tetrahydrofuran (1000 ml) and water (1000 ml) then triethylamine (144 ml) was added. The stuffed solution was cooled to 10C then a solution of ditert-butylcarbonate (224 g) in tetrahydrofuran (1000 ml) was added dropwise over a period of 1hour and the resulting reaction mixture was stirred overnight at room temperature.The solventwas removed in vacuo then the residue was acidified to pH 2-3 with a 2N hydrochloric acid solution. A precipitate was obtained, which was filtered to obtain a white solid. The filtrate was extracted with dichloromethane (6*200 ml). The combined organic layers were dried oversodium sulphate and the solvent evaporated in vacuo.The combined solids were triturated with diethyl ether then filtered and rinsed with cold diethyl ether and dried to afford the title product as a white solid (157 g). ?H-NMR (CDC13, 400 MHz): 5.20 (m, 1H), 4.80 (m, 1H), 4.60 (m, 1H), 4.10 (m, 1H), 1.50 (s, 9H).
  • 90
  • [ 72270-01-0 ]
  • [ 68-41-7 ]
  • 91
  • [ 1885-14-9 ]
  • [ 68-41-7 ]
  • [ 1436857-90-7 ]
  • 92
  • [ 1885-14-9 ]
  • [ 68-41-7 ]
  • [ 1436857-95-2 ]
  • 93
  • [ 937-62-2 ]
  • [ 68-41-7 ]
  • [ 1436857-91-8 ]
Same Skeleton Products
Historical Records

Similar Product of
[ 68-41-7 ]

Chemical Structure| 339-72-0

A185463[ 339-72-0 ]

(S)-4-Aminoisoxazolidin-3-one

Reason: Optical isomers