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[ CAS No. 190900-21-1 ]

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Chemical Structure| 190900-21-1
Chemical Structure| 190900-21-1
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Product Details of [ 190900-21-1 ]

CAS No. :190900-21-1 MDL No. :MFCD04115319
Formula : C10H18N2O3 Boiling Point : 373.1°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :214.26 g/mol Pubchem ID :22617736
Synonyms :

Safety of [ 190900-21-1 ]

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 [ 190900-21-1 ]

  • Upstream synthesis route of [ 190900-21-1 ]
  • Downstream synthetic route of [ 190900-21-1 ]

[ 190900-21-1 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 150008-24-5 ]
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YieldReaction ConditionsOperation in experiment
84% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In tetrahydrofuran; ethyl acetate at 70℃; Inert atmosphere To a solution of ketoxime (0.01 mol) in THF (10 mL) was added T3P (15 mol percent, 50percent soln in EtOAc) and the resulting reaction mixture was stirred at reflux for 1-4 h under nitrogen atmosphere. When the reaction was completed as confirmed by TLC, the solvent was removed under vacuum and the residue was diluted with water (20 mL). The product was extracted with ethyl acetate (2 .x. 20 mL) and the combined organic phase was washed with saturated NaHCO3 solution (1 .x. 10 mL) and brine. The organic phase was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to afford the desired amides in good purity.
48%
Stage #1: With sodium carbonate In water; acetone for 0.0833333 h;
Stage #2: With p-toluenesulfonyl chloride In water; acetone at 20℃;
To a solution of intermediate I-49 (11 g, 50 mmol, 1.0 eq) in acetone (60 mL) was added a solution of Na2CO3 (16 g, 150 mmol, 3.0 eq) in water (80 mL) and the reaction mixture was stirred for 5 minutes. A solution of p-toluenesulfonyl chloride (14 g, 75 mmol, 1.5 eq) in acetone (20 mL) was added slowly and the reaction mixture was stirred at room temperature for 3 hours. Excess solvent was removed by evaporation, water was added and the reaction mixture was extracted with dichloromethane. The combined organic layers were dried over anhydrous MgSO4, the solids were removed by filtration and the filtrate was concentrated by evaporation. The crude reaction product was purified by silica gel column chromatography to give intermediate I-50 (5.0 g, 48percent). MS (ESI): m/z 159.1 (M+H+).
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 10, p. 1074 - 1077
[2] Patent: US2010/204214, 2010, A1, . Location in patent: Page/Page column 108
[3] Patent: WO2006/56877, 2006, A2, . Location in patent: Page/Page column 24
[4] Tetrahedron Letters, 2009, vol. 50, # 2, p. 148 - 151
  • 2
  • [ 34376-54-0 ]
  • [ 24424-99-5 ]
  • [ 190900-21-1 ]
YieldReaction ConditionsOperation in experiment
89% at 10 - 20℃; for 2 h; Intermediate 5 :tert-butyl 5-oxo-l,4-diazepane-l-carboxylate; To a stirred solution of commercially available l,4-diazepan-5-one (3.3 g, 28.94 mmol) in THF cooled to 10°C, was added di-tert-butyl dicarbonate(9.5 g, 43.42 mmol) and the resultant reaction mixture was stirred at RT for 2 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was washed with n-pentane (50 mL) to afford the title compound as a solid (5.5 g, 89percent).:H NMR (300 MHz, DMSO) δ = 7.62 (s, 1H), 3.45-3.40 (m, 4H), 3.12-3.08 (m, 2H), 2.43-2.39 (m, 2H).
795 mg With dmap In dichloromethane at 20℃; for 4 h; 6.01.22.04
5-Oxo-1,4-diazepane-1-carboxylic acid tert-butyl ester
3.26 g di-tert-butyl dicarbonate 160.5 mg DMAP were added to 2,3,6,7-tetrahydro-(1H)-1,4-diazepin-5(4H)-one in 50 mL dichlormethane.
The reaction was stirred 4 h at RT and washed with 10percent citric acid, saturated sodium hydrogencarbonate and saturated sodium chloride solution and evaporated.
The residue was purified by column chromatographie on silica gel (cyclohexane/ethylacetate: 1/1) and crystallized from diethylether/petrolether:3/1 to yield 795 mg of the desired product. Rt: 0.98 min (method B), (M+H)+: 215
795 mg With dmap In dichloromethane at 20℃; for 4 h; 6.01.22.04 5-Oxo- 1 , 4-diazepane- 1 -carboxylic acid tert-butyl ester 3.26 g di-tert-butyl dicarbonate 160.5 mg DMAP were added to 2, 3, 6, 7-tetrahydro-(lH)-l, 4- diazepin-5 (4H)-one in 50 mL dichlormethane. The reaction was stirred 4 h at RT and washed with 10percent) citric acid, saturated sodium hydro gencarbonate and saturated sodium chloride solution and evaporated. The residue was purified by column chromatographie on silica gel (cyclohexane/ ethylacetate: 1/1) and crystallized from diethylether/petrolether: 3/1 to yield 795 mg of the desired product. Rt: 0.98 min (method B), (M+H)+: 215
Reference: [1] Patent: WO2012/3829, 2012, A1, . Location in patent: Page/Page column 59
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 23, p. 5907 - 5911
[3] Patent: US2013/150341, 2013, A1, . Location in patent: Paragraph 0265; 0266
[4] Patent: WO2013/83741, 2013, A1, . Location in patent: Page/Page column 74
  • 3
  • [ 150008-24-5 ]
  • [ 190900-21-1 ]
Reference: [1] Patent: EP1477490, 2004, A1, . Location in patent: Page 109
  • 4
  • [ 190900-20-0 ]
  • [ 24424-99-5 ]
  • [ 190900-21-1 ]
YieldReaction ConditionsOperation in experiment
89% With sodium hydroxide; sodium chloride In chloroform Step B
1-(tert-Butoxycarbonyl)hexahydro-(5H)-1,4-diazepin-5-one
A mixture of hexahydro-(5H)-1,4-diazepin-5-one acetic acid salt (200 mg, 1.15 mmol), di-tert-butyldicarbonate (277 mg, 1.27 mmol) and sodium chloride (460 mg, 7.93 mmol) in 2.0 mL of chloroform was stirred and 2.5 N aqueous sodium hydroxide (460 uL, 1.15 mmol) was added.
The mixture was heated to reflux for 4 h, and then extracted with 3*10 mL of-ethyl acetate.
The combined ethyl acetate extracts were dried over anhydrous sodium sulfate, decanted and evaporated in vacuo to give 219 mg (89percent) of 1-(tert-butoxycarbonyl)hexahydro-(5H)-1,4-diazepin-5-one as a white solid.
1 H NMR (400 MHz, CD3 OD): δ3.60-3.53 (m, 4H), 3.28-3.25 (m, 2H), 2.61-2.56 (m, 2H), 1.47 (s, 9H).
Mass spectrum: m/z=215 (M+1, 100percent). Anal. calcd for C10 H18 N2 O3: C, 56.32; H, 8.04; N, 13.14. Found: C, 55.92; H, 8.48; N, 13.00.
Reference: [1] Patent: US6372733, 2002, B1, . Location in patent: Example 1
[2] Patent: US6043358, 2000, A,
  • 5
  • [ 24424-99-5 ]
  • [ 99822-50-1 ]
  • [ 190900-21-1 ]
Reference: [1] Patent: US2006/25383, 2006, A1, . Location in patent: Page/Page column 71-72
  • 6
  • [ 55186-89-5 ]
  • [ 190900-21-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 23, p. 5907 - 5911
  • 7
  • [ 79099-07-3 ]
  • [ 190900-21-1 ]
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 10, p. 1074 - 1077
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