Sodium Bicarbonate → HCID 67092985, compound

HRID 1261832Notes

Reaction equation

HRID 1261832 reaction equation
O=[C:2]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7][CH2:6][C:3]21[CH2:5][CH2:4]2.COCCN(S(F)(F)[F:27])CCOC.C(=O)(O)[O-].[Na+].[F-:35].[K+]>ClCCCl.C1(C)C=CC=CC=1.[Cl-].C[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC>[F:35][C:2]1([F:27])[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7][CH2:6][C:3]21[CH2:5][CH2:4]2

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 522689Potassium FluorideHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 66783635tert-Butyl 4-oxo-6-azaspiro[2.5]octane-6-carboxylate

Product 1

HCID 67092985HCID 67092985, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 111,2-DichloroethaneSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Silica gel (particle size 32-63 μm, 60 mg) was added to a solution of tert-butyl 4-oxo-6-azaspiro[2.5]octane-6-carboxylate (PCT Int. Appl. WO 2009010429; 1000 mg, 4.44 mmol) in 1,2-dichloroethane (1 ml). Then a solution of bis(2-methoxyethyl)aminosulfur trifluoride (3.1 g, 13.3 mmol) in toluene (3.6 ml) was slowly added. The resulting mixture was heated to 70° C. and was then stirred at this temperature for 6 h. Sodium bicarbonate (74.6 mg, 888 μmol), potassium fluoride (258 mg, 4.44 mmol) and methyltrioctylammonium chloride (179 mg, 444 μmol) were added at 70° C. and the mixture was stirred at 70° C. for an additional 15 h. The mixture was cooled to room temperature and was then quenched in 20% aq. ammonium hydroxide solution (10 ml) while the pH was maintained around 8.5. The organic phase was separated, washed with water, and evaporated. Chromatography (SiO2; heptane→heptane/ethyl acetate 4:1) afforded the title compound (852 mg, 78%). White solid, MS: 248.2 (M+H)+.

Workup

  1. stirringthe mixture was stirred at 70° C. for an additional 15 h
  2. temperatureThe mixture was cooled to room temperature
  3. customwas then quenched in 20% aq. ammonium hydroxide solution (10 ml) while the pH
  4. temperaturewas maintained around 8.5
  5. customThe organic phase was separated
  6. washwashed with water
  7. customevaporated

Sources & evidence

ORD record
ord-d52fc7b2d2ad4f2b9b8391b745f73367
Source dataset
uspto-grants-2013_06
Patent number
US08471004B2

Reaction notes

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