1,2-Dichloroethane → 4-((3-(4-Chlorophenoxy)propylsulfonyl)methyl)tetrahydro-pyran-4-carboxylic acid N-hydroxy amide

HRID 1840513Notes

Reaction equation

HRID 1840513 reaction equation
C(Cl)CCl.[Cl:5][C:6]1[CH:28]=[CH:27][C:9]([O:10][CH2:11][CH2:12][CH2:13][S:14]([CH2:17][C:18]2([C:24](O)=[O:25])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)(=[O:16])=[O:15])=[CH:8][CH:7]=1.[Si]([NH:36][OH:37])(C(C)(C)C)(C)C>ClCCl>[OH:37][NH:36][C:24]([C:18]1([CH2:17][S:14]([CH2:13][CH2:12][CH2:11][O:10][C:9]2[CH:27]=[CH:28][C:6]([Cl:5])=[CH:7][CH:8]=2)(=[O:16])=[O:15])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[O:25]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 99516104-((3-(4-Chlorophenoxy)propylsulfonyl)methyl)-tetrahydropyran-4-carboxylic AcidHCID 17809443t-Butyldimethylsilylhydroxylamine

Product 1

HCID 99085054-((3-(4-Chlorophenoxy)propylsulfonyl)methyl)tetrahydro-pyran-4-carboxylic acid N-hydroxy amideYield 38.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

EDC (40 mg) was added to a solution of Example 13 (75 mg) in dichloromethane (20 ml), followed by tert-butyldimethylsilylhydroxylamine (32 mg) and N,N-dimethylaminopyridine (2 mg), and the resulting clear solution was stirred at room temperature for 3 h. The mixture was then washed with water, saturated bicarbonate and brine, dried over MgSO4 and evaporated. The residue was dissolved in a minimum amount of fresh dichloromethane and 1M aqueous hydrochloric acid in ether (2 ml) was added. The solution was stirred for 10 min, then evaporated and the residue purified by chromatography on silica, eluting with ethyl acetate, to give the title compound (30 mg) as a colourless glass.

Workup

  1. washThe mixture was then washed with water, saturated bicarbonate and brine
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. dissolutionThe residue was dissolved in a minimum amount of fresh dichloromethane and 1M aqueous hydrochloric acid in ether (2 ml)
  5. additionwas added
  6. stirringThe solution was stirred for 10 min
  7. customevaporated
  8. customthe residue purified by chromatography on silica
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-d9258302c3714331b2754e3ce9c2a5eb
Source dataset
uspto-grants-2004_01
Patent number
US06680338B2

Reaction notes

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