Water → HCID 57504574, compound

HRID 1098085Notes

Reaction equation

HRID 1098085 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.O.O.O.[F-].[Si]([O:29][C@@H:30]([CH2:41][CH2:42][N:43]([CH3:45])[CH3:44])[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>[CH3:45][N:43]([CH3:44])[CH2:42][CH2:41][C@H:30]([OH:29])[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 57504576HCID 57504576, compound

Product 1

HCID 57504574HCID 57504574, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammoniumfluoride trihydrate (417 mg, 1.32 mmol) was added to a stirred solution of (2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-(dimethylamino)-N-(5-methylpyridin-2-yl)butanamide (Step 3) (310 mg, 0.88 mmol) in THF (5 mL). The reaction mixture was kept at ambient temperature for 30 minutes. Water and EtOAc were added and the two phases were separated. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with EtOAc/MeOH:10/1) to give the title compound as a solid (110 mg), 1H NMR (300 MHz, CDCl3) δ 9.44 (br s, 1H), 8.15 (d, 1H), 8.12 (d, 1H), 7.51 (dd, 1H), 4.39 (dd, 1H), 2.63 (m, 2H), 2.28 (m, 9H), 2.09 (m, 1H), 1.92 (m, 1H).

Workup

  1. customthe two phases were separated
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified with column chromatography (silica gel, eluting with EtOAc/MeOH:10/1)

Sources & evidence

ORD record
ord-d581c441b7fa456f9598f24ceffddddd
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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