Trifluoroacetic acid → HCID 82293051, compound

HRID 530611Notes

Reaction equation

HRID 530611 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][S:11](=[O:15])(=[O:14])[CH:10]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH3:23][O:22][C:18]1[CH:17]=[C:16]([CH:10]2[S:11](=[O:15])(=[O:14])[CH2:12][CH2:13][NH:8][CH2:9]2)[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118276765HCID 118276765, compound

Product 1

HCID 82293051HCID 82293051, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 150 mL round-bottomed flask, 2-(3-methoxyphenyl)-1,1-dioxo-1λ6-thiomorpholine-4-carboxylic acid tert-butyl ester (435 mg, 1.27 mmol) was combined with dichloromethane (15 ml) to give a light yellow solution. To that was added 4 mL TFA. The resultant reaction mixture was stirred at room temperature for 1 h. Reaction was complete by LCMS. Reaction mixture was concentrated in vacuo. The residue was dissolved in dichloromethane, poured onto 10% NaHCO3 and extracted 3 times with dichloromethane. Combined organic layers were washed with water, dried over Na2SO4, filtered and filtrate concentrated in vacuo to afford 2-(3-methoxyphenyl)-thiomorpholine 1,1-dioxide (252 mg) which was used as is in the next step. (M+H)+=242 m/e.

Workup

  1. customto give a light yellow solution
  2. customThe resultant reaction mixture
  3. customReaction
  4. customReaction mixture
  5. concentrationwas concentrated in vacuo
  6. dissolutionThe residue was dissolved in dichloromethane
  7. additionpoured onto 10% NaHCO3
  8. extractionextracted 3 times with dichloromethane
  9. washCombined organic layers were washed with water
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationfiltrate concentrated in vacuo

Sources & evidence

ORD record
ord-a571db4368f94cec89ef89afa5c221ef
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

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