Diisopropylamine → HCID 178458806, compound

HRID 2075717Notes

Reaction equation

HRID 2075717 reaction equation
N(C(C)C)C(C)C.C([Li])CCC.[S:13]1[CH:17]=[CH:16][N:15]=[C:14]1[SH:18].[F:19][C:20]([F:26])([F:25])[C:21](=[O:24])[CH2:22][CH3:23]>C1COCC1>[F:19][C:20]([F:26])([F:25])[C:21]([C:17]1[S:13][C:14]([SH:18])=[N:15][CH:16]=1)([OH:24])[CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 2382881,1,1-Trifluorobutan-2-oneHCID 178418339ButyllithiumHCID 178527881HCID 178527881, compound

Product 1

HCID 178458806HCID 178458806, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

iPr2NH (2.0 g, 19.9 mmol) was dissolved in THF (23 mL) and cooled to −78° C. n-Butyllithium (2.5M, 8.0 mL, 19.9 mmol) was added dropwise, followed by thiazole-2-thiol (0.9 g, 7.9 mmol) in THF (5 mL). After 10 minutes, trifluoro-2-butanone (0.5 g, 4.0 mmol) was added and the reaction was stirred at −78° C. for 6 hours. The reaction was warmed to room temperature and quenched with 5% aqueous NH4Cl (20 mL). The aqueous layer was acidified and extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (50% EtOAc in hexanes) to give the desired product, 10b.

Workup

  1. additionwas added dropwise
  2. temperatureThe reaction was warmed to room temperature
  3. customquenched with 5% aqueous NH4Cl (20 mL)
  4. extractionextracted with EtOAc
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-336bc8768f0a4388b092edd8a08237d4
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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