Trifluoroacetic acid → 3-(3-Methylphenylsulfonyl)amino-6-isopropyl-1-(carboxymethyl)-2-pyridinone

HRID 993125Notes

Reaction equation

HRID 993125 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[C:13](=[O:29])[N:14]([CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])[C:15]([CH:18]([CH3:20])[CH3:19])=[CH:16][CH:17]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[C:13](=[O:29])[N:14]([CH2:21][C:22]([OH:24])=[O:23])[C:15]([CH:18]([CH3:20])[CH3:19])=[CH:16][CH:17]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 221785803-(3-Methylphenylsulfonyl)amino-6-isopropyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone

Product 1

HCID 221786713-(3-Methylphenylsulfonyl)amino-6-isopropyl-1-(carboxymethyl)-2-pyridinoneYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(3-Methylphenylsulfonyl)amino-6-isopropyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone (1.24 g, 2.95 mmol), as prepared in the preceding step, was dissolved in methylene chloride (20 mL) and reacted with trifluoroacetic acid (8 mL) at ambient temperature for 2 hours. After evaporation in vacuo, the crude product was dissolved in methylene chloride, washed with pH 7 buffer and brine, dried over MgSO4, and filtered. Evaporation of the filtrate gave the title compound (0.72 g, 67%) as a light yellow solid. Mass spectrum (LCMS, ESI) calcd. for C17H20N2O5S: 365.4 (M+H). Found: 365.1.

Workup

  1. customAfter evaporation in vacuo
  2. dissolutionthe crude product was dissolved in methylene chloride
  3. washwashed with pH 7 buffer
  4. dry with materialbrine, dried over MgSO4
  5. filtrationfiltered
  6. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-c9b5f15669524deebe2be31c0e344f7d
Source dataset
uspto-grants-2002_10
Patent number
US06472399B2

Reaction notes

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