Methyl alpha-[2-[[bis[(4-methoxyphenyl)methyl]amino]sulfonyl]ethyl]-2-fluoro-4-nitrobenzeneacetate → Methyl alpha-[2-(aminosulfonyl)ethyl]-2-fluoro-4-nitrobenzeneacetate

HRID 1699654Notes

Reaction equation

HRID 1699654 reaction equation
COC1C=CC(C[N:10](CC2C=CC(OC)=CC=2)[S:11]([CH2:14][CH2:15][CH:16]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:22]=2[F:30])[C:17]([O:19][CH3:20])=[O:18])(=[O:13])=[O:12])=CC=1>C(Cl)Cl.FC(F)(F)C(O)=O>[NH2:10][S:11]([CH2:14][CH2:15][CH:16]([C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:22]=1[F:30])[C:17]([O:19][CH3:20])=[O:18])(=[O:12])=[O:13]

Participants

4

Reactant 1

HCID 18369156Methyl alpha-[2-[[bis[(4-methoxyphenyl)methyl]amino]sulfonyl]ethyl]-2-fluoro-4-nitrobenzeneacetate

Product 1

HCID 18369152Methyl alpha-[2-(aminosulfonyl)ethyl]-2-fluoro-4-nitrobenzeneacetateYield 86.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Methyl .alpha.-[2-[[bis[(4-methoxyphenyl)methyl]amino] sulfonyl]ethyl]-2-fluoro-4-nitrobenzeneacetate (41.6 g, 74.3 mmol) is dissolved in methylene chloride (200 ml) and trifluoroacetic acid (50 ml). The solution is stirred for 2 days then the solvents evaporated. The residue is dissolved in ethyl acetate (750 ml) and washed with sodium bicarbonate solution (200 ml) and brine (100 ml). After drying (MgSO4), filtration and evaporation the title compound is obtained as a solid (20.5 g, 86%) mp 99-101°.

Workup

  1. customthe solvents evaporated
  2. dissolutionThe residue is dissolved in ethyl acetate (750 ml)
  3. washwashed with sodium bicarbonate solution (200 ml) and brine (100 ml)
  4. customAfter drying
  5. filtration(MgSO4), filtration and evaporation the title compound

Sources & evidence

ORD record
ord-b0d4af03584843fd9224c9d406e66a65
Source dataset
uspto-grants-2002_02
Patent number
US06348459B1

Reaction notes

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