Diisopropylamine → HCID 178472193, compound

HRID 2075719Notes

Reaction equation

HRID 2075719 reaction equation
N(C(C)C)C(C)C.C([Li])CCC.[CH3:13][CH2:14][O:15][C:16]([CH3:18])=[O:17].[F:19][C:20]([F:30])([F:29])[C:21]([C:23]1[S:27][C:26]([SH:28])=[N:25][CH:24]=1)=[O:22]>C1COCC1>[CH2:14]([O:15][C:16](=[O:17])[CH2:18][C:21]([OH:22])([C:23]1[S:27][C:26]([SH:28])=[N:25][CH:24]=1)[C:20]([F:29])([F:19])[F:30])[CH3:13]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 8857Ethyl AcetateHCID 178418339ButyllithiumHCID 178519847HCID 178519847, compound

Product 1

HCID 178472193HCID 178472193, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

iPr2NH (205 mg, 2.0 mmol) was dissolved in THF (3.5 mL) and cooled to −10° C. n-Butyllithium (2.5M, 0.81 mL, 2.0 mmol) was added dropwise, and the reaction was cooled to −78° C. EtOAc (179 mg, 2.0 μmmol) in THF (0.5 mL) was added, followed by 10a (188 mg, 0.9 mmol) in THF (10.5 mL), and the reaction was stirred at −78° C. for 1 hour. The reaction was warmed to −10° C. and quenched with 5% aqueous NH4Cl (10 mL). The aqueous layer was extracted with EtOAc, and the combined organic layers were washed with 1N HCl and brine, dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (50% Et2O in hexanes) to give the desired product, 10b.

Workup

  1. additionwas added dropwise
  2. temperatureThe reaction was warmed to −10° C.
  3. customquenched with 5% aqueous NH4Cl (10 mL)
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washthe combined organic layers were washed with 1N HCl and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography (50% Et2O in hexanes)

Sources & evidence

ORD record
ord-d7eade74771040ea98b580918eabb288
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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