Diisopropylethylamine → 2-[4-(4-fluoro-butoxy)-benzenesulfonylamino]-N-hydroxy-acetamide

HRID 722444Notes

Reaction equation

HRID 722444 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][OH:6])=[O:4].[F:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(N(C(C)C)C(C)C)C>ClCCl>[F:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:1][CH2:2][C:3]([NH:5][OH:6])=[O:4])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94811Glycinehydroxamic acidHCID 218848454-(4-Fluorobutoxy)-benzenesulfonyl chloride

Product 1

HCID 218847672-[4-(4-fluoro-butoxy)-benzenesulfonylamino]-N-hydroxy-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the resin from stage 58.1 (350 mg, ˜0.3 mmol) are added successively 4-(4-fluorobutoxy)-benzenesulfonyl chloride (306 mg, 1.15 mmol) in dry dichloromethane (4 ml), and N-ethyldiisopropylamine (0.24 ml, 1.40 mmol) in dry dichloromethane (4 ml). After stirring for 15 h at r.t. the suspension is filtered and the resin washed with dichloromethane (2×), DMF (2×), alternating with H2O and DMF (3×), alternating with THF and 2-propanol (3×), dichloromethane (3×). The resin is dried under reduced pressure to provide polymer-bound 2-[4-(4-fluoro-butoxy)-benzenesulfonylamino]-N-hydroxy-acetamide.

Workup

  1. filtrationis filtered
  2. washthe resin washed with dichloromethane (2×), DMF (2×)
  3. customThe resin is dried under reduced pressure

Sources & evidence

ORD record
ord-787346ec25424e5484a661009f2b3ffd
Source dataset
uspto-grants-2006_11
Patent number
US07138432B1

Reaction notes

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