Trifluoroacetic acid → Methyl(2r)-[4-(2-aminoethoxy)phenyl]({[4(2-butynyloxy)phenyl]sulfonyl}amino)ethanoate

HRID 1976443Notes

Reaction equation

HRID 1976443 reaction equation
C(OC([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C@@H:18]([NH:23][S:24]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]#[C:36][CH3:37])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:13]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C@@H:18]([NH:23][S:24]([C:27]2[CH:28]=[CH:29][C:30]([O:33][CH2:34][C:35]#[C:36][CH3:37])=[CH:31][CH:32]=2)(=[O:26])=[O:25])[C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86590204methyl (2R)-(4-{2-[(tert-butoxycarbonyl)amino]ethoxy}phenyl)({[4-(2-butynyloxy)phenyl]sulfonyl}amino)ethanoate

Product 1

HCID 131722539Methyl(2r)-[4-(2-aminoethoxy)phenyl]({[4(2-butynyloxy)phenyl]sulfonyl}amino)ethanoateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.300 g (0.564 mmol) of methyl (2R)-(4-{2-[(tert-butoxycarbonyl)amino]ethoxy}phenyl)({[4-(2-butynyloxy)phenyl]sulfonyl}amino)ethanoate (from Example 199) in 1.5 mL of dichloromethane was added 1.5 mL of trifluoroacetic acid and the resulting mixture was stirred for 2 h at room temperature and then concentrated in vacuo. The residue was diluted with ethyl acetate and the organics were washed with saturated sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated to provide 0.244 g of methyl(2R)-[4-(2-aminoethoxy)phenyl]({[4-(2-butynyloxy)phenyl]sulfonyl}amino)ethanoate pure enough for use in the next step. Electrospray Mass Spec 433.3 (M+H)+

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washthe organics were washed with saturated sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e8a887ab92344c41a1a1dd8ea9bd9c75
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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