Potassium bisulfate → HCID 57309346, compound

HRID 1682319Notes

Reaction equation

HRID 1682319 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([N:14]1[C@H:18]([CH:19]=[CH:20][CH2:21][CH2:22][C:23](OCC)=[O:24])[CH2:17][O:16][C:15]1([CH3:29])[CH3:28])=[O:13])([CH3:10])([CH3:9])[CH3:8].S([O-])(O)(=O)=O.[K+]>C(OCC)C.O>[C:7]([O:11][C:12]([N:14]1[C@H:18]([CH:19]=[CH:20][CH2:21][CH2:22][CH2:23][OH:24])[CH2:17][O:16][C:15]1([CH3:29])[CH3:28])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 57155621HCID 57155621, compound

Product 1

HCID 57309346HCID 57309346, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

2.7 g of lithium aluminium hydride are added in portions at 0°-2° to a solution of 23.5 g of 2 according to b) in 550 ml of absolute diethyl ether. After stirring at 0°-2° for 3 hours, a solution of 25 g of potassium hydrogen sulphate in 250 ml of water is added dropwise with cooling. The mixture is filtered through Celite® and washed thoroughly with diethyl ether. The organic phase is washed twice with 200 ml of 1 N hydrochloric acid each time and twice with 250 ml of 10% sodium bicarbonate solution each time. The aqueous phases are extracted twice with 100 ml of ether each time. The organic phases are washed with 20% sodium chloride solution, dried over sodium sulphate and concentrated by evaporation. Chromatography on silica gel using ethyl acetate as eluant yields 18.6 g of 3, [α]D =-10.1° (c=1.4, CHCl3); C 15 H27NO4 ; calculated: 63.13%, H 9.54%, N 4.91%; found: C 63.0%, H 9.5%, N 5.0%.

Workup

  1. temperaturewith cooling
  2. filtrationThe mixture is filtered through Celite®
  3. washwashed thoroughly with diethyl ether
  4. washThe organic phase is washed twice with 200 ml of 1 N hydrochloric acid each time
  5. extractionThe aqueous phases are extracted twice with 100 ml of ether each time
  6. washThe organic phases are washed with 20% sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-b0dba3b87c22478a94b6ffba9d164d31
Source dataset
uspto-grants-1992_12
Patent number
US05175344

Reaction notes

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