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

HRID 1662978Notes

Reaction equation

HRID 1662978 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-b003056332d44c048276ff9eafeed7a5
Source dataset
uspto-grants-2011_10
Patent number
US08034810B2

Reaction notes

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