Hydrochloric Acid → 2-{[4-(4-fluorobutoxy)-benzenesulfonyl]-(4-methoxy-benzyl)-amino]-N-hydroxy-acetamide

HRID 722450Notes

Reaction equation

HRID 722450 reaction equation
[F:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([N:16]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[CH2:17][C:18]([NH:20][O:21]C(OCC)(C)C)=[O:19])(=[O:15])=[O:14])=[CH:9][CH:8]=1.Cl>CCOC(C)=O>[F:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([N:16]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[CH2:17][C:18]([NH:20][OH:21])=[O:19])(=[O:15])=[O:14])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866244682-([4-(4-fluorobutoxy)-benzenesulfonyl](4-methoxy-benzyl)amino)-N-(1-ethoxy-1-methyl ethoxy)acetamide

Product 1

HCID 98894442-{[4-(4-fluorobutoxy)-benzenesulfonyl]-(4-methoxy-benzyl)-amino]-N-hydroxy-acetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.22 g of 2-{[4-(4-fluorobutoxy)-benzenesulfonyl](4-methoxy-benzyl)-amino}-N-(1-ethoxy-1-methyl-ethoxy) acetamide in 30 ml of AcOEt is treated with 7 ml of 5N aqueous HCl for 10 min. at r.t. and the mixture is extracted with AcOEt. The combined extracts are washed with sat. NaHCO3 and brine, dried over MgSO4 and concentrated under reduced pressure to give solids which are washed with ether to afford 2-{[4-(4-fluorobutoxy)-benzenesulfonyl]-(4-methoxy-benzyl)-amino]-N-hydroxy-acetamide; NMR (CDCl3): 1.83–2.05 (m, 4H), 3.69 (s, 2H), 3.78 (s, 3H), 4.09 (t, 2H, J=5.56 Hz), 4.25 (s, 2H), 4.48 (t, 1H, J=5.52 Hz), 4.55–4.65 (m, 1H), 6.84 (d, 2H, J=8.56 Hz), 7.00 (d, 2H, J=9.04 Hz), 7.02 (br s, 1H), 7.15 (d, 2H, J=8.56 Hz), 7.77 (d, 2H, J=8.56 Hz), 8.85 (br s, 1H).

Workup

  1. extractionthe mixture is extracted with AcOEt
  2. washThe combined extracts are washed with sat. NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customto give solids which
  6. washare washed with ether

Sources & evidence

ORD record
ord-7db301a1f16347cf818fe71e4e0b75d0
Source dataset
uspto-grants-2006_11
Patent number
US07138432B1

Reaction notes

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