HCID 10132553, compound → HCID 9947270, compound

HRID 2417265Notes

Reaction equation

HRID 2417265 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH:14]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:15]([NH:17][OH:18])=[O:16])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].CO.C1C[O:30]CC1>O>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([S:12]([CH:14]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:15]([NH:17][OH:18])=[O:16])(=[O:30])=[O:13])=[CH:10][CH:11]=1)[C:2]#[C:3][CH3:4]

Participants

4

Reactant 2

HCID 10132553HCID 10132553, compoundHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 9947270HCID 9947270, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 2-{[4-(2-butynyl oxy)phenyl]sulfinyl}-2-cyclohexyl-N-hydroxyacetamide (180 mg, 0.52 mmol) in MeOH/THF at room, wxone (5.0 g, excess) was added in water (20 ml). Reaction mixture was stirred at room temperature for 6 hrs and filtered. Methanol-THF layer was concentrated and extracted with chloroform. The organic layer was washed well with water, dried, filtered and concentrated. The product was purified by silica gel column chromatography by eluting it with 4:1 ethyl acetate; hexane and 2-{[4-(2-butynyl oxy)phenyl]sulfonyl}-2-cyclohexyl-N-hydroxyacetamide was isolated as a white solid. mp: 191° C.; Yield: 45 mg (24%); MS: 366.3 (M+H)+; 1H NMR (300 MHz, DMSO-d6): δ 0.95-1.12 (band, 5H), 1.58 (m, 5H), 1.85 (t, J=2.22 Hz, 3H), 2.05 (m, 1H), 3.63 (d, J=9.1 Hz, 1H), 4.87 (d, J=2.34 Hz, 2H), 7.16 (d, J=9 Hz, 2H), 7.76 (d, J=9 Hz, 2H), 9.01 (s, 1H), 10.7 (s, 1H).

Workup

  1. customReaction mixture
  2. filtrationfiltered
  3. concentrationMethanol-THF layer was concentrated
  4. extractionextracted with chloroform
  5. washThe organic layer was washed well with water
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe product was purified by silica gel column chromatography
  10. washby eluting it with 4:1 ethyl acetate

Sources & evidence

ORD record
ord-2e88d8afbbbc4dcf8cffdbf08db64b60
Source dataset
uspto-grants-2004_11
Patent number
US06825354B2

Reaction notes

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