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Chemical Structure| 1098184-12-3 Chemical Structure| 1098184-12-3
Chemical Structure| 1098184-12-3

(S)-2-(((Benzyloxy)carbonyl)amino)-2-(tetrahydro-2H-pyran-4-yl)acetic acid

CAS No.: 1098184-12-3

4.5 *For Research Use Only !

Cat. No.: A382343 Purity: 95%

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Product Details of [ 1098184-12-3 ]

CAS No. :1098184-12-3
Formula : C15H19NO5
M.W : 293.32
SMILES Code : O=C(O)[C@@H](NC(OCC1=CC=CC=C1)=O)C2CCOCC2
MDL No. :MFCD29038835
InChI Key :VTENIAVLDXOKCR-ZDUSSCGKSA-N
Pubchem ID :66926961

Safety of [ 1098184-12-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 1098184-12-3 ]

* 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 [ 1098184-12-3 ]

[ 1098184-12-3 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 1098184-12-3 ]
  • (3S,8aR)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]octahydropyrrolo[1,2-a]pyrazine-3-carboxamide dihydrochloride [ No CAS ]
  • [ 1266229-19-9 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃; for 18.0h;Product distribution / selectivity; tert-Butyl(3S,8aR)-3-[(1R)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamoyl]hexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate (380 mg) obtained in Example 5 (ii) was dissolved in 4M hydrogen chloride-ethyl acetate solution (5 mL), and the solution was stirred at room temperature for 18 hr. The precipitate resulting from the reaction mixture was collected by filtration. To the collected precipitate were added tetrahydrofuran (5 mL), N-ethyl-N-(1-methylethyl)propan-2-amine (0.497 mL), <strong>[1098184-12-3](2S)-[(benzyloxy)carbonyl]amino}(tetrahydro-2H-pyran-4-yl)ethanoic acid</strong> (418 mg) and 1-hydroxybenzotriazole (218 mg). To this mixture was added 1-ethyl-3-3-dimethylaminopropyl)carbodiimide hydrochloride (310 mg), and the mixture was stirred at room temperature for 18 hr. To the reaction mixture was added water (50 mL), and the mixture was extracted with ethyl acetate (200 mL). The organic layer was washed with saturated brine (50 mL), dried over anhydrous magnesium sulfate, and filtered, and the filtrate was concentrated to give an oil. This oil (500 mg) was dissolved in methanol (3 mL), 20% palladium-carbon (100 mg, 20 wt %) was added thereto, and the mixture was stirred at room temperature for 4 hr under a hydrogen atmosphere (3 atm). The insoluble material was filtered off through a celite pad, and the filtrate was concentrated to give an oil.
  • 2
  • [ 1098184-12-3 ]
  • C17H23N3O2*(x)ClH [ No CAS ]
  • [ 1266230-03-8 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 18.0h; tert-Butyl(3S,8aR)-3-[(4R)-3,4-dihydro-2H-chromen-4-ylcarbamoyl]hexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate (450 mg) was dissolved in ethyl acetate (3 mL), 4M hydrogen chloride-ethyl acetate solution (3 mL) was added thereto, and the mixture was stirred at room temperature for 1 hr. The mixture was concentrated under reduced pressure, and the residue was collected by filtration, washed with ether, and dried under reduced pressure to give a colorless amorphous powder (410 mg). The obtained colorless amorphous powder (200 mg), <strong>[1098184-12-3](2S)-[(benzyloxy)carbonyl]amino}(tetrahydro-2H-pyran-4-yl)ethanoic acid</strong> (235 mg), O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (406 mg) and N,N-diisopropylethylamine (0.558 mL) were mixed in N,N-dimethylformamide (5 mL), and the mixture was stirred at room temperature for 18 hr. The mixture was diluted with ethyl acetate (30 mL), and washed with water (30 mL), saturated aqueous sodium hydrogen carbonate solution (50 mL) and saturated brine (50 mL). The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=15/85?100/0) to give the title compound (200 mg) as a colorless amorphous powder. LC-MS: 577 (MH+)
  • 3
  • [ 1098184-12-3 ]
  • C17H22FN3O*(x)ClH [ No CAS ]
  • [ 1266231-06-4 ]
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 3.0h; To tert-butyl(3S,8aR)-3-[(1S,2S)-2-fluoro-2,3-dihydro-1H-inden-1-yl]carbamoyl}hexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate (300 mg) were added ethyl acetate (1.5 mL) and 4M hydrogen chloride-ethyl acetate solution (6.0 mL), and the mixture was stirred at room temperature for 1 hr, and concentrated under reduced pressure. To the residue was added ethyl acetate, and the precipitate was collected by filtration, washed with ethyl acetate, and dried in vacuum for 30 min. The obtained residue was dissolved in N,N-dimethylformamide (6.0 mL), N,N-diisopropylethylamine (0.78 mL), <strong>[1098184-12-3](2S)-[(benzyloxy)carbonyl]amino}(tetrahydro-2H-pyran-4-yl)ethanoic acid</strong> (283 mg), 1-hydroxybenzotriazole (141 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (285 mg) were successively added thereto, and the mixture was stirred at room temperature for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50?0/100). The object fractions were collected, and concentrated under reduced pressure, and the residue was dried in vacuum for 1 hr to give the title compound (249 mg) as a white powder.1H NMR (DMSO-d6, 300 MHz): delta 1.15-1.42 (4H, m), 1.48-2.21 (8H, m), 2.90-3.90 (9H, m), 4.09-4.57 (2H, m), 4.80-5.41 (5H, m), 7.11-7.40 (9H, m), 7.46-7.63 (1H, m), 8.12-8.31 (1H, m).
  • 4
  • [ 1098184-12-3 ]
  • C17H21F2N3O2*(x)ClH [ No CAS ]
  • [ 1266231-15-5 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 16.0h; tert-Butyl(3S,8aR)-3-[(4R)-3,4-dihydro-2H-chromen-4-ylcarbamoyl]-7,7-difluorohexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate (400 mg) was dissolved in 4M hydrogen chloride-ethyl acetate solution (4.0 mL), and the solution was stirred at room temperature for 30 min, and concentrated under reduced pressure. To the residue was added ethyl acetate (10 mL), and the mixture was stirred at room temperature for 20 min. The precipitate was collected by filtration, washed with ethyl acetate/diethyl ether (=1/1), and dried in vacuum for 30 min. The obtained powder was dissolved in N,N-dimethylformamide (8.0 mL), <strong>[1098184-12-3](2S)-[(benzyloxy)carbonyl]amino}(tetrahydro-2H-pyran-4-yl)ethanoic acid</strong> (375 mg) and N,N-diisopropylethylamine (1.27 mL) were added thereto. Then, O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (695 mg) was added thereto, and the mixture was stirred at room temperature for 16 hr. To the reaction mixture was added ethyl acetate/water, and the organic layer was separated. The organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=70/30?0/100). The object fractions were collected, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30?0/100). The object fractions were collected, the solvent was evaporated under reduced pressure, and the residue was dried in vacuum for 1 hr to give the title compound (201 mg) as a white powder.LC-MS: 613.3 (MH+).1H NMR (DMSO-d6, 300 MHz): delta 1.20-1.69 (4H, m), 1.74-2.09 (4H, m), 2.13-2.73 (5H, m), 3.12-3.94 (6H, m), 4.08-4.57 (4H, m), 4.83-5.09 (4H, m), 6.70-6.88 (2H, m), 7.07-7.62 (8H, m), 8.11-8.27 (1H, m).
  • 6
  • [ 1098184-12-3 ]
  • [ 1266230-10-7 ]
  • [ 1266230-03-8 ]
  • 7
  • [ 1098184-12-3 ]
  • (3S,8aR)-2[(2S)-2-amino-2-(tetrahydro-2H-pyran-4-yl)acetyl]-N-[(4R)-3,4-dihydro-2H-chromen-4-yl]-octahydropyrrolo[1,2-a]pyrazine-3-carboxamide dihydrochloride [ No CAS ]
  • 8
  • [ 1098184-12-3 ]
  • [ 1266230-05-0 ]
  • 9
  • [ 1098184-12-3 ]
  • (3S,8aR)-N-[(4R)-3,4-dihydro-2H-chromen-4-yl]-2-[(2S)-2-[(N-methyl-L-alanyl)amino]-2-(tetrahydro-2H-pyran-4-yl)acetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxamide dihydrochloride [ No CAS ]
 

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