HCID 86754371, compound → HCID 21224176, compound

HRID 1584400Notes

Reaction equation

HRID 1584400 reaction equation
C1O[C:4]([NH:29][OH:30])([CH2:5][C:6]2([S:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]2)[O:3]C1>CC(C)=O.Cl>[O:22]([C:19]1[CH:18]=[CH:17][C:16]([S:13]([C:6]2([CH2:5][C:4]([NH:29][OH:30])=[O:3])[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]2)(=[O:15])=[O:14])=[CH:21][CH:20]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 1

HCID 86754371HCID 86754371, compound

Product 1

HCID 21224176HCID 21224176, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

Following the procedure outlined in Example 15A, N-hydroxy-2-[4-(4-phenoxyphenylsulfonyl)-cyclohexanone-4-yl]-acetamide ethylene ketal (400 mg) was prepared from the corresponding N-tert-butoxy precursor. The above product was dissolved in a 1:1 mixture of acetone and 1M hydrochloric acid (40 ml) and stirred at room temperature for 18 hours. The reaction was concentrated under reduced pressure and extracted with ethyl acetate. Silica gel chromatography using 10% methanol/methylene chloride gave 2-[4-(4-phenoxyphenylsulfonyl)cyclohexanone-4-yl]-N-hydroxyacetamide as a white solid: m.p. 106° C. (dec), m/e=404 (MH+, FABMS).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-7ef6b55a83d549e38534901a7426d661
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

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