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

HRID 2414612Notes

Reaction equation

HRID 2414612 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C@H:16]([C:21]2[CH:37]=[CH:36][C:24]([O:25][CH2:26][CH2:27][NH:28]C(=O)OC(C)(C)C)=[CH:23][CH:22]=2)[C:17](NO)=[O:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].FC(F)(F)[C:40](O)=[O:41]>ClCCl>[NH2:28][CH2:27][CH2:26][O:25][C:24]1[CH:23]=[CH:22][C:21]([C@@H:16]([NH:15][S:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:1][C:2]#[C:3][CH3:4])=[CH:7][CH:8]=2)(=[O:14])=[O:13])[C:17]([O:41][CH3:40])=[O:18])=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54233279tert-butyl 2-{4-[(1R)-1-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-2-(hydroxyamino)-2-oxoethyl]phenoxy}ethylcarbamate

Product 1

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

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-751af38a2eb747a48f26ba3778c41308
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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