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[ CAS No. 138650-24-5 ] {[proInfo.proName]}

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Chemical Structure| 138650-24-5
Chemical Structure| 138650-24-5
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CAS No. :138650-24-5 MDL No. :MFCD12547198
Formula : C4H7NO3 Boiling Point : No data available
Linear Structure Formula :- InChI Key :LXRNYRAHXDUNKR-UHFFFAOYSA-N
M.W : 117.10 Pubchem ID :15024256
Synonyms :

Safety of [ 138650-24-5 ]

Signal Word:Warning Class:
Precautionary Statements:P305+P351+P338 UN#:
Hazard Statements:H302-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 138650-24-5 ]

* 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 [ 138650-24-5 ]

[ 138650-24-5 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 138650-24-5 ]
  • [ 82911-69-1 ]
  • [ 1380327-56-9 ]
YieldReaction ConditionsOperation in experiment
Intermediate 8; 3-(9H-Fluoren-9-ylmethoxycarbonylamino)-oxetane-3-carboxylic acid A solution of (9H-fluoren-9-yl)methyl 2,5-dioxopyrrolidin-1-yl carbonate (3.2 g, 9.5 mmol) in dioxane (30 ml) was added to a solution of <strong>[138650-24-5]3-amino-oxetane-3-carboxylic acid</strong> (1.17 g, 10 mmol) [CAS 138650-24-5; Synlett 1991, 783-784] and potassium carbonate (2.76 g, 20.0 mmol) in water (30 ml). The light yellow opaque solution was stirred at room temperature for 75 minutes. During that time, a white solid precipitated. The mixture was diluted with water and extracted two times with diethyl ether. The white solid did not dissolve and was kept therefore in the aqueous layer, which was acidified to pH 2 by addition of 1N HCl and extracted three times with EtOAc. The combined EtOAc layers were washed with brine, dried with Na2SO4 and evaporated.The crude title compound was obtained as white solid and was used without further purification.
Intermediate 8 3-(9H-Fluoren-9-ylmethoxycarbonylamino)-oxetane-3-carboxylic acidA solution of (9H-fluoren-9-yl)methyl 2,5-dioxopyrrolidin-l-yl carbonate (3.2 g, 9.5 mmol) in dioxane (30 ml) was added to a solution of <strong>[138650-24-5]3-amino-oxetane-3-carboxylic acid</strong> (1.17 g, 10 mmol) [CAS 138650-24-5; Synlett 1991, 783-784] and potassium carbonate (2.76 g, 20.0 mmol) in water (30 ml). The light yellow opaque solution was stirred at room temperature for 75 minutes. During that time, a white solid precipitated. The mixture was diluted with water and extracted two times with diethyl ether. The white solid did not dissolve and was kept therefore in the aqueous layer, which was acidified to pH 2 by addition of IN HC1 and extracted three times with EtOAc. The combined EtOAc layers were washed with brine, dried with Na2S04 and evaporated.The crude title compound was obtained as white solid and was used without further purification.
With potassium carbonate; In 1,4-dioxane; water; at 20℃; for 1.25h;Inert atmosphere; GammaAlpha1 3-(9H-Fluoren-9-ylmethoxycarbonylamino)-oxetane-3-carboxylic acidA solution of (9H-fluoren-9-yl)methyl 2,5-dioxopyrrolidin-l-yl carbonate (3.2 g, 9.5 mmol) in dioxane (30 ml) was added to a solution of <strong>[138650-24-5]3-amino-oxetane-3-carboxylic acid</strong> (1.17 g, 10 mmol) and potassium carbonate (2.76 g, 20.0 mmol) in water (30 ml). The light yellow opaque solution was stirred at room temperature for 75 minutes. During that time, a white solid precipitated. The mixture was diluted with water and extracted two times with diethyl ether. The white solid did not dissolve and was kept therefore in the aqueous layer, which was acidified to pH 2 by addition of IN HC1 and extracted three times with EtOAc. The combined EtOAc layers were washed with brine, dried with Na2S04 and evaporated. The crude title compound was obtained as white solid and was used without further purification.
With potassium carbonate; In 1,4-dioxane; water; at 20℃; for 1.25h;Inert atmosphere; [A] 3-(9H-Fluoren-9-ylmethoxycarbonylamino)-oxetane-3-carboxylic acid A solution of (9H-fluoren-9-yl)methyl 2,5-dioxopyrrolidin-1-yl carbonate (3.2 g, 9.5 mmol) in dioxane (30 ml) was added to a solution of <strong>[138650-24-5]3-amino-oxetane-3-carboxylic acid</strong> (1.17 g, mmol) and potassium carbonate (2.76 g, 20.0 mmol) in water (30 ml). The light yellow opaque solution was stirred at room temperature for 75 minutes. During that time, a white solid precipitated. The mixture was diluted with water and extracted two times with diethyl ether. The white solid did not dissolve and was kept therefore in the aqueous layer, which was acidified to pH 2 by addition of 1N HCl and extracted three times with EtOAc. The combined EtOAc layers were washed with brine, dried with Na2SO4 and evaporated. The crude title compound was obtained as white solid and was used without further purification.

  • 2
  • [ 24424-99-5 ]
  • [ 138650-24-5 ]
  • [ 1159736-25-0 ]
YieldReaction ConditionsOperation in experiment
88% With tetramethyl ammoniumhydroxide; In acetonitrile; at 50℃; for 12h; A mixture of <strong>[138650-24-5]3-aminooxetane-3-carboxylic acid</strong> (800 mg, 6.83 mmol), tetramethylammonium hydroxide (507 mg, 5.56 mmol), di-tert-butyl dicarbonate (1640 mg, 7.51 mmol) in acetonitrile (30 mL) was stirred for 12 hours at 50 C. The mixture was concentrated and the residue was purified by flash column chromatography to afford 3- ((tert-butoxycarbonyl)amino)oxetane-3-carboxylic acid (1.3 g, 88% yield). LCMS m/z = 218.1 [M+H]+.
87% With triethylamine; sodium hydroxide; In methanol; water; at 20℃; for 16h; A solution of <strong>[138650-24-5]3-aminooxetane-3-carboxylic acid</strong> SM 1 (0.23 g, 2 mmol) and (Boc)20 (872mg, 4 mmol) in MeOH (10 mL) and TEA (1 mL) was NaOH (2 mL, iN in water), stirred at RT for16 h. Quenched with water, extracted with EtOAc, then then the water layer was adjusted pH to 23 with HC1 (2 N), extracted with EtOAc and dried, concentrated under reduced pressure to givecompound 1(0.38 g, 87%). LC-MS: m/z =118.1 [M+H-Boc]
38% With sodium hydroxide; In water; for 18h; To l-aminooxetane-3-carboxylic acid (1.00 g, 8.54 mmol, 1 eq.) in dioxane (15 mL, 0.5 M) was added a solution of sodium hydroxide (1.55 g, 38.7 mmol, 4.5 eq.) in water (15 mL) followed by di-ZerZ-butyl dicarbonate (2.09 g, 9.29 mmol, 1.1 eq.) A white solid formed. The reaction was stirred for 18 hours and then concentrated in vacuo. The residue was taken up in ethyl acetate and washed with 1 M aqueous hydrochloric acid solution and with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to give 71 (633 mg, 38%) as a white solid. *H NMR (400 MHz, DMSO-<), presumed to be a mixture of rotamers: delta 12.93 (br s, 1H), 7.59 and 7.93 (2 br s, total 1H), 4.71-4.78 (m, 2H), 4.47 (d, J=6.4 Hz, 2H), 1.30 and 1.38 (2 s, total 9H).
With tetramethyl ammoniumhydroxide; In acetonitrile; at 20℃; A mixture of <strong>[138650-24-5]3-aminooxetane-3-carboxylic acid</strong> (117.0 mg, 1.0 mmol) and NMe4OH.5H2O (TMAH) (181.0 mg, 1.0 mmol) in CH3CN (10 mL) was stirred at room temperature for 30 minutes. Then (Boc)2O (327.3 mg, 1.5 mmol) was added and the resulting mixture was stirred overnight. Water (10 mL) was added and the mixture was extracted with ether (20 mL). The aqueous layer was acidified to pH=2 by addition of citric acid (solid) and extracted with EtOAc (2×20 mL). The organic layers were combined, dried over Na2SO4, filtered and concentrated to yield crude 3-((tert-butoxycarbonyl)amino)oxetane-3-carboxylic acid (45) which was used without further purification. MS m/z 218.1 (M+1)+.
A mixture of <strong>[138650-24-5]3-aminooxetane-3-carboxylic acid</strong> (1 17.0 mg, 1 .0 mmol) and NMe4OH-5H20 (TMAH) (181 .0 mg, 1 .0 mmol) in CH3CN (10 mL) was stirred at room temperature for 30 minutes. Then (Boc)20 (327.3 mg, 1 .5 mmol) was added and the resulting mixture was stirred overnight. Water (10 mL) was added and the mixture was extracted with ether (20 mL). The aqueous layer was acidified to pH=2 by addition of citric acid (solid) and extracted with EtOAc (2x20 mL). The organic layers were combined, dried over Na2S04, filtered and concentrated to yield crude 3-((feri-butoxycarbonyl)amino)oxetane-3- carboxylic acid (45) which was used without further purification. MS m/z 218.1 (M+1 ) +. Carbonyl diimidazole (CDI) (162.2 mg, 1 .0 mmol) was added to a stirred solution of 3- ((feri-butoxycarbonyl)amino)oxetane-3-carboxylic acid (45) (217.1 mg, 1 .0 mmol) ) in NMP (1 .0 mL). After 20 minutes, N-(5-(N'-hydroxycarbamimidoyl)-2- methylphenyl)imidazo[1 ,2-a]pyridine-3-carboxamide (9) (150.0 mg, 0.5 mmol) was added in one portion and the resulting solution was stirred for 1 hour before it was heated at 125 C for 15 minutes in a microwave reactor. The reaction solution was subjected to standard aqueous work up to afford a residue which was purified by silicachromatography to yield terf-butyl (3-(3-(3-(imidazo[1 ,2-a]pyridine-3-carboxamido)-4- methylphenyl)-1 ,2,4-oxadiazol-5-yl)oxetan-3-yl)carbamate (46) (159 mg, 65% yield). MS m/z 491 .2 (M+1 ) +. (3-(3-(3-(lmidazo[1 ,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1 ,2,4-oxadiazol-5- yl)oxetan-3-yl)carbamate (46) (29.5 mg, 0.06 mmol) was dissolved in TFA (0.5 mL) and stirred at room temperature for 10 minutes. Then TFA was removed under vacuum to yield crude N-(5-(5-(3-aminooxetan-3-yl)-1 ,2,4-oxadiazol-3-yl)-2- methylphenyl)imidazo[1 ,2-a]pyridine-3-carboxamide (47) as a TFA salt which was used without further purification. MS m/z 391 .1 (M+1 ) +.

  • 3
  • [ 138650-24-5 ]
  • 2-fluoro-4-iodo-N-methyl-N-[2-(trimethylsilyl)ethoxymethyl]benzamide [ No CAS ]
  • 3-(3-fluoro-4-{methyl-[2-(trimethylsilyl)ethoxymethyl]carbamoyl}phenylamino)oxetane-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% The mixture of compound 40(500 mg, 1.22 mmol), 3-minooxetane-3-carboxylic acid (57)(215 mg, 1.84 mmol) [38], K2CO3 (590 mg, 4.27 mmol), CuI (47 mg,0.24 mmol) and 1 drop of Et3N dissolved in DMF (4 mL) and water(1 mL) was stirred for 15 min, then 2-acetylcyclohexanone (190 mg,1.35 mmol) was added and the mixture was stirred for 15 h at100. After cooling the mixture was rotovapped and subjected toHPLC with neutral mobile phase to afford 340 mg (70%) of 3-(3-fluoro-4-{methyl-[2-(trimethylsilyl)ethoxymethyl]carbamoyl}phenylamino)oxetane-3-carboxylic acid (58). MS (ESI) [MH]399. 1H NMR (400 MHz, DMSO-d6) d 7.61 (m, 1H), 7.53 (t, J 8.8 Hz,1H), 6.21 (d, J 8.4 Hz, 1H), 5.96 (d, J 13.6 Hz, 1H), 4.97 (d,J 6.0 Hz, 2H), 4.55 (d, J 6.0 Hz, 2), 2.73 (d, J 4.4 Hz, 3), 2.21(m, 2), 1.12 (m, 2), 0.14 (s, 9). The mixture of compound 40(500 mg, 1.22 mmol), 3-minooxetane-3-carboxylic acid (57)(215 mg, 1.84 mmol),38 K2CO3 (590 mg, 4.27 mmol), CuI (47 mg,0.24 mmol) and 1 drop of Et3N dissolved in DMF (4 mL) and water(1 mL) was stirred for 15 min, then 2-acetylcyclohexanone (190 mg,1.35 mmol) was added and the mixture was stirred for 15 h at100. After cooling the mixture was acidified with hydrochloricacid to pH 3 and extracted with ethyl acetate. The organic layerwas washed with cold water, with brine, dried over Na2SO4 and thesolvent evaporated under reduced pressure to give 287 mg (88%) of3-[3-fluoro-4-(methylcarbamoyl)phenylamino]oxetane-3-carboxylic acid (59). MS (ESI) [MH] 269. 1H NMR (400 MHz,DMSO-d6), d 7.69 (m, 1H), 7.48 (t, J 8.8 Hz, 1H), 6.15 (d, J 8.4 Hz,1H), 5.96 (d, J 13.6 Hz, 1H), 4.97 (d, J 6.0 Hz, 2H), 4.55 (d,J 6.0 Hz, 2), 2.73 (d, J 4.4 Hz, 3). Sodium hydride (66 mg,1.65 mmol, 60% in oil) was added at 0 to the solution of compound58 (600 mg, 1.5 mmol) in DMF (6 mL). The resulting mixturewas stirred for 0.5 h keeping same temperature. After the reactionwas completed, iodomethane (0.14 mL, 2.25 mmol) was added tothe mixture and stirring was continued for 6 h at 0. Finally, thesolution was accurately poured into cold water, extracted withethyl acetate, dried over Na2SO4 and rotovapped. The obtainedcrude methyl 3-(3-fluoro-4-{methyl-[2-(trimethylsilyl)ethoxymethyl]carbamoyl}phenylamino)oxetane-3-carboxylate (60)was subjected to HPLC with mobile phase containing 0.1% of TFA toafford 46 mg (11%) of methyl 3-[3-fluoro-4-(methylcarbamoyl)phenylamino]oxetane-3-carboxylate (61). MS (ESI) [MH] 283.1H NMR (400 MHz, CDCl3) d 7.96 (t, J 9.2 Hz, 1), 6.60 (brs, 1),6.31 (dd, J1 8.8 Hz, J2 2.0 Hz, 1), 6.12 (dd, J1 14.4 Hz,J2 2.0 Hz, 1), 5.13 (d, J 6.4 Hz, 2), 5.03 (brs, 1), 4.76 (d,J 6.4 Hz, 2), 3.84 (s, 3), 3.01 (d, J 4.4 Hz, 3). Compound 42(63 mg, 0.276 mmol) was added to the solution of compound 59 or61 (0.25 mmol) in DMF (1 mL). The resulting mixturewas stirred for12 h at 80 under argon atmosphere. After the reaction wascompleted, the solutionwas poured into cold water, extracted withethyl acetate, dried over Na2SO4 and rotovapped. Separation byHPLC afforded 17 mg (16%) of N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[3-fluoro-4-(methylcarbamoyl)phenylamino]oxetane-3-carboxamide (62).MS (ESI) [MH] 437. 1H NMR (400 MHz, DMSOd6)d 10.59 (s, 1), 8.30 (s, 1), 8.16 (d, J 8.8 Hz, 1), 8.08 (d,J 8.4 Hz, 1), 7.73 (m, 1), 7.55 (s, 1), 7.49 (t, J 8.4 Hz, 1), 6.23(d, J 10.0 Hz, 1), 6.10 (d, J 13.6 Hz, 1), 5.09 (d, J 6.8 Hz, 2),4.59 (d, J 6.4 Hz, 2), 2.70 (d, J 4.0 Hz, 3).
  • 4
  • [ 138650-24-5 ]
  • [ 143782-23-4 ]
  • 1-[4-cyano-3-(trifluoromethyl)phenyl]-4-(hydroxymethyl)-2-thioxoimidazolidine-4-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% In acetonitrile; for 18h; Compound 42(228 mg, 1 mmol) was added to the solution of compound 57(117 mg, 1 mmol) in acetonitrile (3 mL). The resulting mixture wasstirred for 18 h (LC-MS control). The solventwas removed followingthe standard procedure and the product was subjected to HPLC togive 159 mg (46%) of 63. MS (ESI) [MH] 346. 1H NMR (DMSO-d6)d 12.73 (brs, 1), 10.35 (brs, 1), 8.17 (s, 1), 8.02 (d, J 8.0 Hz, 1),5.17 (brs, 2), 3.72 (t, J 11.2 Hz, 2), 3.62 (d, J 10.0 Hz, 1), 3.46(d, J 11.6 Hz, 1). 13 NMR (90 MHz, DMSO-d6) d 136.42, 132.40,131.98, 131.56, 131.15, 124.37, 120.74, 116.13, 99.71, 64.65, 35.72.
  • 5
  • [ 138650-24-5 ]
  • 9H-fluoren-9-ylmethyl 4-[3-[2-[(3,4-dichlorophenyl)methylamino]-2-oxoethyl]-4-oxoquinazolin-6-yl]piperazine-1-carboxylate [ No CAS ]
  • 2-[6-[4-(3-aminooxetane-3-carbonyl)piperazin-1-yl]-4-oxoquinazolin-3-yl]-N-[(3,4-dichlorophenyl)methyl]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
11% To a solution of 9H-fluoren-9-ylmethyl 4-[3-[2-[(3,4-dichlorophenyl)methylamino]-2-oxoethyl]-4-oxoquinazolin-6-yl]piperazine-1-carboxylate (intermediate A-5) (30 mg, 0.044 mmol) in dry DMF (1 mL) was added a solution of methanamine (2 mL, 16.0 mmol; 8.0 M solution in ethanol; [CAS RN 74-89-5]) and stirring at rt continued overnight. The crude reaction mixture was concentrated under reduced pressure and redissolved in THF (2 mL). To this solution were added PYBOP (28.6 mg, 0.055 mmol; [CAS RN 128625-52-5]) and DIPEA (12 muL, 0.066 mmol) under an atmosphere of nitrogen. Then, <strong>[138650-24-5]3-aminooxetane-3-carboxylic acid</strong> (6.4 mg, 0.055 mmol; [CAS RN 138650-24-5]) was added and the reaction mixture stirred at rt overnight. Purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile- water provided the title compound as colorless oil (2.6 mg, 11 %). MS: m/e = 545.3 [M+H]+.
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