Water → HCID 57504572, compound

HRID 1098080Notes

Reaction equation

HRID 1098080 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.O.O.O.[F-].[Si]([O:29][C@H:30]([CH2:41][CH3:42])[C:31]([NH:33][C:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][N:35]=1)=[O:32])(C(C)(C)C)(C)C.O.CCOC(C)=O>C1COCC1>[OH:29][C@H:30]([CH2:41][CH3:42])[C:31]([NH:33][C:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][N:35]=1)=[O:32]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 57504573HCID 57504573, compound

Product 1

HCID 57504572HCID 57504572, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammoniumfluoride trihydrate (3.21 g, 10.19 mmol) was added to a stirred solution of (2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-N-(5-methylpyridin-2-yl)butanamide (Step 2) (2.00 g, 6.79 mmol) in THF (20 mL). The reaction mixture was kept at ambient temperature for 2 hrs. Water and EtOAc were added and the two phases were separated. The aqueous phase was extracted with EtOAc. The organic extracts were combined and washed with water, dried over MgSO4 and concentrated in vacuo. The residue was recrystallised from diethyl ether to give the title compound as colourless crystals (1.14 g).

Workup

  1. customthe two phases were separated
  2. extractionThe aqueous phase was extracted with EtOAc
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallised from diethyl ether

Sources & evidence

ORD record
ord-c2978fe54bd74e379fcf08aec2660653
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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