Water → HCID 57656165, compound

HRID 911276Notes

Reaction equation

HRID 911276 reaction equation
Br[C:2](C)(C)C(Br)=O.[F:8][C:9]([F:23])([F:22])[C:10]([NH:12][CH2:13][C:14]1[CH:19]=C[C:17](OC)=[CH:16][CH:15]=1)=[O:11].[C:24]([CH:27]([CH:29]([C:31]([O-])=O)[OH:30])[OH:28])([O-])=O.[Na+].[K+].O>ClCCCl.[Fe](Cl)(Cl)Cl.CCOC(C)=O>[CH3:2][C:27]1([CH3:24])[C:29](=[O:30])[C:31]2[CH:19]=[C:14]([CH2:13][NH:12][C:10](=[O:11])[C:9]([F:8])([F:22])[F:23])[CH:15]=[CH:16][C:17]=2[O:28]1

Participants

8

Reactant 4

HCID 962WaterHCID 886852-Bromo-2-methylpropionyl bromideHCID 885647HCID 885647, compoundHCID 9855836Potassium sodium tartarate

Product 1

HCID 57656165HCID 57656165, compoundYield 17%

Reagents, catalysts & solvents 3

HCID 24380Iron chloride (FeCl3)CatalystHCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add 2-bromoisobutyryl bromide (1.724 g, 7.5 mmol) to a solution of 2,2,2-trifluoro-N-(4-methoxy-benzyl)-acetamide (1.166 g, 5.0 mmol) in 1,2-dichloroethane (8 mL) at 15° C., then add powdered anhydrous iron(III) chloride (973 mg, 6.0 mmol). Stir the reaction at 15° C. for 3 h and at ambient temperature for 8 days. Add dropwise saturated aqueous potassium sodium tartrate, then water and EtOAc, and stir for 1 h. Filter off the solid, separate the organic layer, and extract the aqueous layer three times with EtOAc. Combine the organic extracts, wash with brine, dry over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with EtOAc/hexane (1:3) to give the desired intermediate (253 mg, 17%).

Workup

  1. additionadd
  2. customthe reaction at 15° C. for 3 h
  3. filtrationFilter off the solid
  4. customseparate the organic layer
  5. extractionextract the aqueous layer three times with EtOAc
  6. washwash with brine
  7. dry with materialdry over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo
  10. customPurify by chromatography on silica gel eluting with EtOAc/hexane (1:3)

Sources & evidence

ORD record
ord-815d8448594749638f0c7f0c0f67ac02
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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