Diisopropylamine → HCID 86701943, compound

HRID 715770Notes

Reaction equation

HRID 715770 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18]([OH:20])=[O:19].[CH3:21][C:22]([S:25]([N:27]=[C:28]1[CH2:31][O:30][CH2:29]1)=[O:26])([CH3:24])[CH3:23]>O1CCCC1>[CH3:23][C:22]([CH3:24])([S:25]([NH:27][C:28]1([C:17]2[S:13][C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH:16]=2)[CH2:31][O:30][CH2:29]1)=[O:26])[CH3:21]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 107002-Thiophenecarboxylic acidHCID 468399952-Methyl-N-(oxetan-3-ylidene)propane-2-sulfinamideHCID 178418339Butyllithium

Product 1

HCID 86701943HCID 86701943, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Butyllithium (6.16 ml, 15.41 mmol) was added dropwise to a stirred solution of diisopropylamine (1.919 ml, 13.69 mmol) in tetrahydrofuran (10 ml) at −78° C. The solution was allowed to warm to room temperature and then added dropwise by syringe to a stirred −78° C. solution of thiophene-2-carboxylic acid (0.877 g, 6.85 mmol) in tetrahydrofuran (30 ml). The resulting suspension was stirred for 40 minutes at −78° C. when a solution of 2-methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide (1 g, 5.71 mmol) in tetrahydrofuran (10 ml) was added dropwise. After the addition was complete, the reaction mixture was allowed to warm to room temperature, quenched with saturated ammonium chloride and diluted with a water to dissolve the remaining solids. The aqueous solution was extracted with ethyl acetate, adjusted to pH 2 by addition of 1N aqueous hydrochloric acid and re-extracted with ethyl acetate and methylene chloride. The organic extracts were dried with magnesium sulfate, filtered, concentrated and purified by normal phase chromatography to give the title compound.

Workup

  1. additionwas added dropwise
  2. additionAfter the addition
  3. temperatureto warm to room temperature
  4. customquenched with saturated ammonium chloride
  5. additiondiluted with a water
  6. dissolutionto dissolve the remaining solids
  7. extractionThe aqueous solution was extracted with ethyl acetate
  8. additionadjusted to pH 2 by addition of 1N aqueous hydrochloric acid
  9. extractionre-extracted with ethyl acetate and methylene chloride
  10. dry with materialThe organic extracts were dried with magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. custompurified by normal phase chromatography

Sources & evidence

ORD record
ord-709a0b8f10e04476b1b4258031c78164
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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