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Chemical Structure| 54043-71-9

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Product Details of [ 54043-71-9 ]

CAS No. :54043-71-9
Formula : C7H12O4
M.W : 160.17
SMILES Code : O=C(O)C(C)(C)CC(OC)=O
MDL No. :MFCD16619681
InChI Key :MUXJXSWYXDORJN-UHFFFAOYSA-N
Pubchem ID :12602176

Safety of [ 54043-71-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P280-P305+P351+P338-P310

Application In Synthesis of [ 54043-71-9 ]

* 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.

  • Upstream synthesis route of [ 54043-71-9 ]

[ 54043-71-9 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 67-56-1 ]
  • [ 597-43-3 ]
  • [ 54043-71-9 ]
YieldReaction ConditionsOperation in experiment
51%
Stage #1: at 0 - 20℃; for 16 h;
Stage #2: With hydrogenchloride In water
Compound 365l-(4-((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2- yl)methyI)(methyl)amin -2-methylbutan-2-yl)-3-(4-(tert-butyl)phenyl)ureaStep 1. Preparation of 4-methoxy-2,2-dimethyl-4-oxo-butanoic acidTo a stirred solution of 2,2-dimethylbutanedioic acid (4.5 g, 31mmol) in MeOH (45 mL) was added 98percent H2S04 (0.45 mL) dropwise at 0° C. Then the reaction mixture was stirred at rt for 16 h. The solution was concentrated. Then saturated aqueous NaHC03 (20 mL) was added to the residue and washed with hexane (50 mL x 3). Then 6N HCl was added to the aqueous phase until pH=2, extracted with EA (200 mL x 4), dried with Na2S04 and concentrated to afford the title compound (2.5 g, yield 51percent) as a colorless oil without purification. 1H NMR (500MHz, CDC13): δ 3.65 (s, 3H), 2.61 (s, 2H), 1.27 (s, 6H) ppm.
23% at 20℃; Cooling with ice An ice-cold solution of commercially available compound 135 (50 g, 342 mmol), and methanol (277 mL) was treated dropwise with sulfuric acid (3.36 g, 34.2 mmol) over 10 min then warmed to r.t. gradually overnight. Most of the solvent was removed by rotary evaporation, then saturated aqueous NaHC03 was carefully added. The pH of the solution was adjusted to 1.9 by addition of 1 M HC1 then extracted into EtOAc (200 mL), washed with diluted brine (50 mL), dried (MgS04), filtered and reduced to 29 g of colorless oil. Column chromatography gave pure compound 136 as a colorless solid (12.5 g, 23 percent).
References: [1] Patent: WO2012/82436, 2012, A2, . Location in patent: Page/Page column 275.
[2] Patent: WO2014/12081, 2014, A2, . Location in patent: Paragraph 0017; 00110.
[3] Journal of the Chemical Society, 1904, vol. 85, p. 539.
[4] Bulletin de la Societe Chimique de France, 1964, p. 828 - 830.
  • 2
  • [ 597-43-3 ]
  • [ 54043-71-9 ]
YieldReaction ConditionsOperation in experiment
91.8 mmol, 67% With hydrogenchloride; sulfuric acid In methanol Step C:
2,2-Dimethylbutanedioic acid, 4-methyl ester
2,2-dimethylsuccinic acid (20 g, 137 mmol) dissolved in 200 ml absolute methanol at 0° was treated dropwise with 2 mL concentrated sulfuric acid.
After the addition was complete, the mixture was allowed to warm to room temperature and stirred for 16 hours.
The mixture was concentrated in vacuo to 50 mL and slowly treated with 200 mL of saturated aqueous sodium bicarbonate.
The mixture was washed with hexane (3*) and the aqueous layer removed and cooled in an ice bath.
The mixture was acidified to pH 2 by slow addition of 6N HCl then extracted with ether (8*).
The combined extracts were washed with brine, dried over magnesium sulfate, filtered and solvents removed in vacuo.
The residue was dried at room temperature under vacuum to afford 14.7 g (91.8 mmol, 67percent) of a viscous oil that slowly solidified upon standing.
1 H NMR analysis indicates the product is a mixture of the title compound and 15percent of the isomeric 2,2-dimethylbutanedioic acid, 1-methyl ester. NMR (200 MHz, CDCl3) of title compound: 1.29 (s,6H), 2.60 (s,2H), 3.66 (s,3H). NMR (200 MHz, CDCl3) of isomer: 1.28 (s,6H), 2.63 (s,2H), 3.68 (s,3H).
91.8 mmol, 67% With hydrogenchloride; sulfuric acid In methanol Step A
2,2-Dimethylbutanedioic acid, 4-methyl ester
2,2-Dimethylsuccinic acid (20 g, 140 mmol) dissolved in 200 mL of absolute methanol at 0° was treated dropwise with 2 mL of concentrated sulfuric acid.
After the addition was complete, the mixture was allowed to warm to room temperature and stirred for 16 hours.
The mixture was concentrated under vacuum to 50 mL and slowly treated with 200 mL of saturated aqueous sodium bicarbonate.
The mixture was washed with hexane (3*) and the aqueous layer removed and cooled in an ice bath.
The mixture was acidified to pH 2 by slow addition of 6 N HCl then extracted with ether (8*).
The combined extracts were washed with brine, dried over magnesium sulfate, filtered and solvents removed under vacuum.
The residue was dried at room temperature under vacuum to afford 14.7 g (91.8 mmol, 67percent) of a viscous oil that slowly solidified upon standing.
91.8 mmol, 67% With hydrogenchloride; sulfuric acid In methanol Step J
2,2-Dimethylbutanedioic acid, 4-methyl ester
2,2-Dimethylsuccinic acid (20 g, 137 mmol) dissolved in 200 mL of absolute methanol at 0° C. was treated dropwise with 2 mL of concentrated sulfuric acid.
After the addition was complete, the mixture was allowed to warm to room temperature and stir for 16 hours.
The mixture was concentrated under vacuum to 50 mL and slowly treated with 200 mL of saturated aqueous sodium bicarbonate.
The mixture was washed with hexane (3*) and the aqueous layer removed and cooled in an ice bath.
The mixture was acidified to pH 2 by slow addition of 6N HCl then extracted with ether (8*).
The combined extracts were washed with brine, dried over magnesium sulfate, filtered and solvents removed under vacuum.
The residue was dried at room temperature under vacuum to afford 14.7 g (91.8 mmol, 67percent) of the product as a viscous oil that slowly solidified upon standing. 1 H NMR (200 MHz, CDCl3): 1.29 (s, 6H), 2.60 (s, 2H), 3.65 (s, 3H).
References: [1] Patent: US5206235, 1993, A, .
[2] Patent: US5672596, 1997, A, .
[3] Patent: US5726319, 1998, A, .
  • 3
  • [ 67-56-1 ]
  • [ 17347-61-4 ]
  • [ 54043-71-9 ]
References: [1] Patent: WO2014/153667, 2014, A1, . Location in patent: Page/Page column 59; 103.
  • 4
  • [ 67-56-1 ]
  • [ 597-43-3 ]
  • [ 54043-71-9 ]
  • [ 32980-26-0 ]
References: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 10, p. 1716 - 1728.
  • 5
  • [ 96-32-2 ]
  • [ 79-31-2 ]
  • [ 54043-71-9 ]
References: [1] Synthesis, 1980, # 9, p. 710 - 713.
 

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