Potassium hydroxy sulfite → HCID 68904327, compound

HRID 2198261Notes

Reaction equation

HRID 2198261 reaction equation
[CH2:1]([NH:4][C:5]([C:7]1[C:15]2[CH2:14][CH2:13]S[CH2:11][C:10]=2[S:9][C:8]=1[NH:16][C:17]([CH:19]1[C:21]([CH3:23])([CH3:22])[C:20]1([CH3:25])[CH3:24])=[O:18])=[O:6])[CH2:2][CH3:3].O[O:27][S:28]([O-:30])=O.[K+]>CC(C)=O.C(OCC)(=O)C>[CH2:1]([NH:4][C:5]([C:7]1[C:15]2[CH2:14][CH2:13][S:28](=[O:30])(=[O:27])[CH2:11][C:10]=2[S:9][C:8]=1[NH:16][C:17]([CH:19]1[C:20]([CH3:25])([CH3:24])[C:21]1([CH3:23])[CH3:22])=[O:18])=[O:6])[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 68904159HCID 68904159, compound

Product 1

HCID 68904327HCID 68904327, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 133D (0.16 g, 0.41 mmol) in 40 mL acetone was added OXONE® (1 g, 1.29 mmol) in one portion. The resulting suspension was allowed to stir at room temperature for 16 hours. The reaction was diluted with ethyl acetate and washed with water (2×), brine (1×), dried (MgSO4), filtered and concentrated. The crude material was chromatographed (15% ethyl acetate/hexanes) to afford the title compound. 1H NMR (500 MHz, dimethylsulfoxide-d6) δ ppm 0.81-0.97 (m, 3H) 1.10-1.30 (m, 12H) 1.39-1.66 (m, 3H) 3.09-3.25 (m, 4H) 3.36 (t, J=6.10 Hz, 2H) 4.41 (s, 2H) 7.93 (t, J=5.49 Hz, 1H) 10.83 (s, 1H). MS (ESI+) m/z 413.1 (M+H)+. Anal. calcd. for C19H28N2O4S2: C, 55.31; H, 6.84; N, 6.79. Found: C, 55.31; H, 7.13; N, 6.54.

Workup

  1. washwashed with water (2×), brine (1×)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was chromatographed (15% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-955c42647e724a51a402f302d8eb8434
Source dataset
uspto-grants-2012_12
Patent number
US08338623B2

Reaction notes

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