Trifluoroacetic anhydride → HCID 18612732, compound

HRID 1264584Notes

Reaction equation

HRID 1264584 reaction equation
O[CH2:2][CH:3]([N:8]([S:23]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[C:4]([O:6][CH3:7])=[O:5].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[CH3:33][O:32][C:29]1[CH:30]=[CH:31][C:26]([S:23]([N:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:17](=[O:22])[C:18]([F:19])([F:21])[F:20])[C:3](=[CH2:2])[C:4]([O:6][CH3:7])=[O:5])(=[O:24])=[O:25])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 18612733HCID 18612733, compound

Product 1

HCID 18612732HCID 18612732, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.0 g (2.54 mmol) of methyl 3-hydroxy-2-{(4-methoxybenzenesulfonyl)-[2-(2,2,2-trifluoroacetylamino)benzyl]amino}propionate in 10 ml of CH2Cl2 was added 1.8 ml (12.7 mmol) of trifluoroacetic anhydride. After 1 hour at room temperature, the solvent was removed. Dichloromethane was added several times and the solvent removed under vacuum after each addition. Methanol was then added 2 times and the solvent removed under vacuum to give methyl 2-{(4-methoxybenzenesulfonyl)-[2-(2,2,2-trifluoroacetylamino)benzyl]-amino}acrylate as a glass. The glass was dissolved in methanol and 0.213 g of anhydrous NaHCO3 was added. The mixture was stirred at room temperature overnight and concentrated under vacuum to dryness. To the residue was added ethyl acetate and water. The organic layer was separated, washed with H2O, brine and dried with Na2SO4. The solvent was removed and the residue (1.0 g) was chromatographed on silica gel thick layer plates with hexane-ethyl acetate (1:1) as solvent to give 0.365 g of product as a glass. Anal. for C20H19F3N2O6S: Calc'd: C, 50.9; H, 4.1; N, 5.9; F, 12.1; S, 6.7; Found: C, 50.8; H, 4.4; N, 5.5; F, 11.7; S, 6.7.

Workup

  1. customthe solvent was removed
  2. additionDichloromethane was added several times
  3. customthe solvent removed under vacuum
  4. additionafter each addition
  5. additionMethanol was then added 2 times
  6. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-6a29af12fdbb4756a991d1c54912e247
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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