Water → HCID 57504567, compound

HRID 1098069Notes

Reaction equation

HRID 1098069 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.O.O.O.[F-].[Si]([O:29][CH:30]([CH2:41][CH2:42][S:43]([CH3:46])(=[O:45])=[O:44])[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][CH:30]([CH2:41][CH2:42][S:43]([CH3:46])(=[O:45])=[O:44])[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 57504568HCID 57504568, compound

Product 1

HCID 57504567HCID 57504567, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammoniumfluoride trihydrate (1.43 g, 4.54 mmol) was added to a stirred solution of 2-{[tert-butyl(dimethyl)silyl]oxy}-N-(5-methylpyridin-2-yl)-4-(methylsulfonyl)butanamide (Step 3) (1.17 g, 3.03 mmol) in THF (10 mL). The reaction mixture was kept at ambient temperature for 30 minutes. 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 EtOAc to give the title compound as colourless solid (0.57 g), 1H NMR (500 MHz, DMSO) δ 8.14 (d, 1H), 7.99 (d, 1H), 7.62 (dd, 1H), 4.23 (m, 1H), 3.17 (m, 2H), 2.96 (s, 3H), 2.24 (s, 3H), 2.16 (m, 1H), 1.98 (m, 1H).

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 EtOAc

Sources & evidence

ORD record
ord-0b32897ce1184d8ab7ffec633196055b
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

Loading…