Pivaloyl chloride → HCID 58483373, compound

HRID 1846105Notes

Reaction equation

HRID 1846105 reaction equation
FC(F)(F)C(=N[Si](C)(C)C)O[Si](C)(C)C.[NH2:16][CH2:17][C:18]1[C:19]([Cl:28])=[C:20]([C:24]([F:27])=[CH:25][CH:26]=1)[C:21]([OH:23])=[O:22].[C:29](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])=[O:30]>C1COCC1>[Cl:28][C:19]1[C:18]([CH2:17][NH:16][C:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[O:30])=[CH:26][CH:25]=[C:24]([F:27])[C:20]=1[C:21]([OH:23])=[O:22]

Participants

5

Reactant 3

HCID 62493Pivaloyl chlorideHCID 94358Bis(trimethylsilyl)trifluoroacetamideHCID 58483350HCID 58483350, compound

Product 1

HCID 58483373HCID 58483373, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

BSTFA (0.18 mL; 1.15 mmol) was added to a mixture of 3-aminomethyl-2-chlor-6-fluorobenzoic acid (270 mg; 1.12 mmol, HCl-salt) in 8 mL THF, it was stirred at reflux for 20 min, and then cooled in an ice bath. TEA (0.783 mL; 5.62 mmol) and Piv-Cl (142 μL; 1.16 mmol) in 2 mL THF were added and it was stirred overnight. The solvent was removed i.vac. and the residue was diluted with water and 10 mL HOAc, extracted (3×) with DCM, dried over Na2SO4 and concentrated i vac.

Workup

  1. temperatureat reflux for 20 min
  2. temperaturecooled in an ice bath
  3. stirringit was stirred overnight
  4. customThe solvent was removed i.vac
  5. additionand the residue was diluted with water and 10 mL HOAc
  6. extractionextracted (3×) with DCM
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated i vac

Sources & evidence

ORD record
ord-05fbe026978841d2b4cc664f4201a8ae
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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