Sodium Hydroxide → HCID 67144853, compound

HRID 1968611Notes

Reaction equation

HRID 1968611 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][N:21]2[CH2:26][CH2:25][NH:24][C:23](=O)[CH:22]2[CH:28]([CH3:30])[CH3:29])=[CH:10][CH:9]=1.[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.CCOCC.O>[C:14]1([C:11]2[CH:12]=[CH:13][CH:8]=[CH:9][CH:10]=2)[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH:22]1[CH:28]([CH3:30])[CH3:29]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydride2×HCID 67145356HCID 67145356, compound

Product 1

HCID 67144853HCID 67144853, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.0M solution of lithium aluminum hydride in tetrahydrofuran (4.8 mL, 4.8 mmol) was cooled to 0°, then a solution of EXAMPLE 12B (0.45 g, 1.31 mmol) in tetrahydrofuran (9 mL) was added dropwise. The reaction was stirred at room temperature overnight. The next day more lithium aluminum hydride solution was added (4.8 mL, 4.8 mmol) and the reaction stirred at room temperature for another two days. The reaction was then cooled to 0° and water (0.75 mL) was carefully added, followed by 4N NaOH (0.75 mL), and additional water (2.2 mL). Na2SO4 and ether (25 mL) were added, and after stirring for 45 minutes ; the mixture was filtered through Celite® (diatomaceous earth). Concentration of the filtrate gave the title compound.

Workup

  1. stirringthe reaction stirred at room temperature for another two days
  2. temperatureThe reaction was then cooled to 0°
  3. stirringafter stirring for 45 minutes
  4. filtrationthe mixture was filtered through Celite® (diatomaceous earth)

Sources & evidence

ORD record
ord-e546071f419144e1b514e0a6a8cfa038
Source dataset
uspto-grants-2013_04
Patent number
US08426422B2

Reaction notes

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